CN101410437A - Curable resin, curable resin compositions and moldings thereof - Google Patents
Curable resin, curable resin compositions and moldings thereof Download PDFInfo
- Publication number
- CN101410437A CN101410437A CNA2007800106023A CN200780010602A CN101410437A CN 101410437 A CN101410437 A CN 101410437A CN A2007800106023 A CNA2007800106023 A CN A2007800106023A CN 200780010602 A CN200780010602 A CN 200780010602A CN 101410437 A CN101410437 A CN 101410437A
- Authority
- CN
- China
- Prior art keywords
- curable resin
- general formula
- structural unit
- silane
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 45
- 239000011347 resin Substances 0.000 title claims abstract description 45
- 239000011342 resin composition Substances 0.000 title claims description 25
- 238000000465 moulding Methods 0.000 title description 6
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 16
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 10
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000012856 packing Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 17
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 230000003301 hydrolyzing effect Effects 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000010354 integration Effects 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 239000011521 glass Substances 0.000 abstract description 11
- 229920003023 plastic Polymers 0.000 abstract description 6
- 239000004033 plastic Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 3
- -1 3-methacryloxypropyl Chemical group 0.000 description 62
- 238000010438 heat treatment Methods 0.000 description 21
- 229920002554 vinyl polymer Polymers 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229920002050 silicone resin Polymers 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-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
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000005357 flat glass Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 150000003377 silicon compounds Chemical class 0.000 description 4
- 125000005504 styryl group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- HCOKJWUULRTBRS-UHFFFAOYSA-N propan-2-yloxysilane Chemical compound CC(C)O[SiH3] HCOKJWUULRTBRS-UHFFFAOYSA-N 0.000 description 3
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 description 2
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 2
- GNRBSDIBKIHSJH-UHFFFAOYSA-N butyl(tripropoxy)silane Chemical compound CCCC[Si](OCCC)(OCCC)OCCC GNRBSDIBKIHSJH-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- YCEQUKAYVABWTE-UHFFFAOYSA-N dichloro-methyl-prop-2-enylsilane Chemical compound C[Si](Cl)(Cl)CC=C YCEQUKAYVABWTE-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920005669 high impact polystyrene Polymers 0.000 description 2
- 239000004797 high-impact polystyrene Substances 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000012780 transparent material Substances 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical group C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 1
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- OKQXCDUCLYWRHA-UHFFFAOYSA-N 3-[chloro(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)Cl OKQXCDUCLYWRHA-UHFFFAOYSA-N 0.000 description 1
- CSBJCQMIXISILC-UHFFFAOYSA-N 3-[chloro(dimethyl)silyl]propyl prop-2-enoate Chemical compound C[Si](C)(Cl)CCCOC(=O)C=C CSBJCQMIXISILC-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- HIKAXIZBPOCKKQ-UHFFFAOYSA-N 3-[dimethyl(propan-2-yloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(C)O[Si](C)(C)CCCOC(=O)C(C)=C HIKAXIZBPOCKKQ-UHFFFAOYSA-N 0.000 description 1
- HWMSQFUYMBPRHY-UHFFFAOYSA-N 3-[dimethyl(propan-2-yloxy)silyl]propyl prop-2-enoate Chemical compound CC(C)O[Si](C)(C)CCCOC(=O)C=C HWMSQFUYMBPRHY-UHFFFAOYSA-N 0.000 description 1
- JUINTNKGYWNEDR-UHFFFAOYSA-N 3-[dimethyl(propoxy)silyl]propyl prop-2-enoate Chemical compound CCCO[Si](C)(C)CCCOC(=O)C=C JUINTNKGYWNEDR-UHFFFAOYSA-N 0.000 description 1
- JSOZORWBKQSQCJ-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(C)CCCOC(=O)C(C)=C JSOZORWBKQSQCJ-UHFFFAOYSA-N 0.000 description 1
- DGBFOBNYTYHFPN-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propyl prop-2-enoate Chemical compound CCO[Si](C)(C)CCCOC(=O)C=C DGBFOBNYTYHFPN-UHFFFAOYSA-N 0.000 description 1
- ZCRUJAKCJLCJCP-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(C)CCCOC(=O)C=C ZCRUJAKCJLCJCP-UHFFFAOYSA-N 0.000 description 1
- AJYYIXLOZNDFHC-UHFFFAOYSA-N 3-[methyl(dipropoxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CCCO[Si](C)(OCCC)CCCOC(=O)C(C)=C AJYYIXLOZNDFHC-UHFFFAOYSA-N 0.000 description 1
- UMZKIKYKUFCIEG-UHFFFAOYSA-N 3-[methyl-di(propan-2-yloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(C)O[Si](C)(OC(C)C)CCCOC(=O)C(C)=C UMZKIKYKUFCIEG-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- DOGMJCPBZJUYGB-UHFFFAOYSA-N 3-trichlorosilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](Cl)(Cl)Cl DOGMJCPBZJUYGB-UHFFFAOYSA-N 0.000 description 1
- LEPRPXBFZRAOGU-UHFFFAOYSA-N 3-trichlorosilylpropyl prop-2-enoate Chemical compound Cl[Si](Cl)(Cl)CCCOC(=O)C=C LEPRPXBFZRAOGU-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- TUHZDSBERNZREI-UHFFFAOYSA-N 4-[dichloro(methyl)silyl]butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC[Si](C)(Cl)Cl TUHZDSBERNZREI-UHFFFAOYSA-N 0.000 description 1
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- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 1
- QABJMCUIZVKWCF-UHFFFAOYSA-N methyl-di(propan-2-yloxy)silicon Chemical compound CC(C)O[Si](C)OC(C)C QABJMCUIZVKWCF-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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- FABOKLHQXVRECE-UHFFFAOYSA-N phenyl(tripropoxy)silane Chemical group CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1 FABOKLHQXVRECE-UHFFFAOYSA-N 0.000 description 1
- XHTWKNPMPDIELI-UHFFFAOYSA-N phenylmethoxysilane Chemical compound [SiH3]OCC1=CC=CC=C1 XHTWKNPMPDIELI-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 239000005053 propyltrichlorosilane Substances 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- GXMNGLIMQIPFEB-UHFFFAOYSA-N tetraethoxygermane Chemical compound CCO[Ge](OCC)(OCC)OCC GXMNGLIMQIPFEB-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- ACOVYJCRYLWRLR-UHFFFAOYSA-N tetramethoxygermane Chemical compound CO[Ge](OC)(OC)OC ACOVYJCRYLWRLR-UHFFFAOYSA-N 0.000 description 1
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- TTYRJPILQGWBOQ-UHFFFAOYSA-N trichloro(cyclohex-3-en-1-yl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCC=CC1 TTYRJPILQGWBOQ-UHFFFAOYSA-N 0.000 description 1
- SIPHWXREAZVVNS-UHFFFAOYSA-N trichloro(cyclohexyl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCCCC1 SIPHWXREAZVVNS-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- YHVKBMGCQCHIMZ-VOTSOKGWSA-N trichloro-[(e)-2-phenylethenyl]silane Chemical compound Cl[Si](Cl)(Cl)\C=C\C1=CC=CC=C1 YHVKBMGCQCHIMZ-VOTSOKGWSA-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
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 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
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- HUZZQXYTKNNCOU-UHFFFAOYSA-N triethyl(methoxy)silane Chemical compound CC[Si](CC)(CC)OC HUZZQXYTKNNCOU-UHFFFAOYSA-N 0.000 description 1
- UCUKUIPXDKEYLX-UHFFFAOYSA-N triethyl(propan-2-yloxy)silane Chemical compound CC[Si](CC)(CC)OC(C)C UCUKUIPXDKEYLX-UHFFFAOYSA-N 0.000 description 1
- RXJWOBGGPLEFEE-UHFFFAOYSA-N triethyl(propoxy)silane Chemical compound CCCO[Si](CC)(CC)CC RXJWOBGGPLEFEE-UHFFFAOYSA-N 0.000 description 1
- JRSJRHKJPOJTMS-MDZDMXLPSA-N trimethoxy-[(e)-2-phenylethenyl]silane Chemical compound CO[Si](OC)(OC)\C=C\C1=CC=CC=C1 JRSJRHKJPOJTMS-MDZDMXLPSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- FBGNFSBDYRZOSE-UHFFFAOYSA-N tris(ethenyl)-ethoxysilane Chemical compound CCO[Si](C=C)(C=C)C=C FBGNFSBDYRZOSE-UHFFFAOYSA-N 0.000 description 1
- JYTZMGROHNUACI-UHFFFAOYSA-N tris(ethenyl)-methoxysilane Chemical compound CO[Si](C=C)(C=C)C=C JYTZMGROHNUACI-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/58—Metal-containing 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
- 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
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
A curable resin which exhibits strength, transparency, heat resistance and dimensional stability which are equivalent to those of inorganic glass respectively as well as high toughness and fabricability which are equivalent to those of plastics respectively. A curable resin having a molecular structure of the general formula (1) consisting of dense structural units (A) and thin structural units (B), in which the dense structural units (A) consist of a metal oxide having a Kp value of 0.68 to 0.8 and the thin structural units (B) have Kp values of less than 0.68 and comprises an organic substance and an organometallic oxide, with each Kp value being calculated by free volume fraction according to the formula (2), and which has an (A)/(B) weight ratio is 0.01 to 5.00, at least one unsaturated bond, and a number-average molecular weight of 800 to 60000: -{(A)-(B)m}n- (1), Kp=An*Vw*p/Mw (2) wherein An is Avogadro's number; Vw is van der Waals volume; p is density; and Mw is molecular weight.
Description
Technical field
The present invention relates to access the curable resin of the formed body that has such high tenacity of the such intensity of unorganic glass, the transparency, thermotolerance and dimensional stability and plastics and processibility simultaneously, relate to and to access and in the window material of the optical applications of for example lens, CD, optical fiber and flat display substrate etc., various conveying machinery, dwelling house etc. etc., to use, can possess the curable resin of the formed body of lightweight, high impact and the transparency.
Background technology
As transparent material, excellences such as the thermotolerance of unorganic glass, dimensional stability are utilized in wide industrial field.Though unorganic glass has such advantageous feature, exist as inferior shortcoming: proportion weighs more than 2.5, lacking toughness and not shock-resistant and easy to be broken, poor in processability.The material of glass as an alternative, the needs of polystyrene, PMMA transparent plasticss such as (polymethylmethacrylates) are also increasing, though their lightweights and excellent in workability, but owing to be organism, therefore exist thermotolerance, photostabilization, dimensional stability etc. and glassy phase than significance difference, the problem that purposes is restricted.
Be not limited to glass, plastics, the material system at general homogeneous realizes that with high level all rerum naturas such as thermotolerance, shock resistance, physical strength are difficult.As the method that addresses this problem, known under the situation that Young's modulus, intensity, thermotolerance etc. are reduced, the HIPS (high-impact polystyrene) that shock resistance has been carried out improving waits the method for the polymer alloy that is representative.But the specific refractory power of blended resin exists the transparency significantly to worsen such problem not simultaneously.In addition, by in resin, adding inorganic powder, fiber, can carry out reinforcement to Young's modulus, dimensional stability, but under the situation of keeping the transparency, add difficulty, owing to cooperating inorganic powder that resin viscosity is increased, therefore become the material that lacks processibility.
As the method that addresses this problem, because metal and nonmetal intermediary characteristic that Siliciumatom has, the silicone resin of thermotolerance, weathering resistance and water tolerance aspect excellence becomes hope.But, in the silicone resin, do not have yet and have high strength and flexible material simultaneously, high-intensity silicone resin is owing to a little close structural unit of free body integration rate by cross-linking density height, inhibition molecular motion constitutes, therefore crisp, being difficult to forming process is heavy wall, and its purposes is limited in coating agent etc.Present situation is the silicone resin that is used for the moulding purposes, rests on the low intensive silicon rubber that only low by cross-linking density, as to suppress the binding force of the molecule big thin structural unit of free body integration rate constitutes.
Patent documentation 1: specially permit communique No. 3598749
Patent documentation 2: the spy opens the 2006-22207 communique
Patent documentation 3: the spy opens the 2005-330455 communique
Summary of the invention
The problem that invention will solve
Therefore, the object of the present invention is to provide and to have the such high tenacity of the such intensity of unorganic glass, the transparency, thermotolerance and dimensional stability and plastics and the curable resin and the composition thereof of processibility simultaneously.
Be used to solve the method for problem
The present inventor studies repeatedly in order to solve above-mentioned problem, found that the curable resin that has different close structural unit of free body integration rate and thin structural unit in the molecular structure can form the molded object of curable resin of the purposes that is suitable for replacing the excellent unorganic glass of the transparency, thereby finished the present invention.
Promptly, the present invention relates to have the curable resin of organo-metallic structure, this curable resin has the molecular structure that comprises close structural unit (A) and thin structural unit (B) shown in the following general formula (1), it is characterized in that: close structural unit (A) is to contain the structural unit that packing coefficient Kp is 0.68～0.8 metal oxide, and this packing coefficient Kp is calculated by free body integration rate and obtained by following calculating formula (2); Dredge structural unit (B) and be above-mentioned packing coefficient Kp less than 0.68, contain organism and organo-metallic oxide compound and the structural unit that constitutes; The weight ratio of structural unit (A)/(B) is 0.01～5.00; And have at least one unsaturated link(age), molecular-weight average is 800～60000.
-{(A)-(B)
m}
n- (1)
(wherein, m and n represent the integer more than 1).
Kp＝An·Vw·p/Mw (2)
[wherein, An=N, Vw=Van der waals volumes, p=density, Mw=molecular weight, Vw=∑ Va, Va=4 π/R
3-∑ 1/3 π hi
2(3Ra-hi), hi=Ra-(Ra
2+ di
2-Ri
2)/2di, the Ra=atomic radius, Ri=is in conjunction with atomic radius and di=interatomic distance].
At this, close structural unit (A) comprises the metal oxide position that does not comprise the three-dimensional polyhedral structure skeleton of having of organism position of following general formula (I), dredging structural unit (B) and comprise the chain unit that is made of the organo-metallic oxide compound shown in the following general formula (II) and the organism position of general formula (I), is the preferred scheme of curable resin of the present invention.
(RSiO
3/2)
w(MO
2)
x(RXSiO)
y(XMO
3/2)
z (I)
(R
3R
4R
5SiO
1/2)
j(R
6R
7SiO)
k{R
6R
7XSiO
1/2}
1 (II)
[wherein, R is (a)-R
1-OCO-CR
2=CH
2, (b)-R
1-CR
2=CH
2Or (c)-CH=CH
2Unsaturated group, alkyl, cycloalkyl, cycloalkenyl group, phenyl, hydrogen atom, alkoxyl group or the alkyl siloxy of expression, a plurality of R can differ from one another in the formula (I), but at least 1 comprises above-mentioned (a) and (b) or (c) any, R
1Expression alkylidene group, alkylidene or phenylene, R
2The expression hydrogen or alkyl.In addition, R
3～R
7Be (a)-R
1-OCO-CR
2=CH
2, (b)-R
1-CR
2=CH
2Or (c)-CH=CH
2Unsaturated group, alkyl, cycloalkyl, cycloalkenyl group, phenyl, hydrogen atom, alkoxyl group or the alkyl siloxy of expression.In addition, M is the atoms metal of silicon, germanium, titanium or zirconium, and X is halogen atom or alkoxyl group, and w is the integer more than 4, and x, y and z are the integers that satisfies w+x+y+z 〉=8.J, k and 1 represent the integer more than 0 respectively].
In addition, above-mentioned general formula (I) is by RSiX
3, MX
4Or the hydrolytic condensate of their mixture (wherein R, M are identical during with general formula (I) with X) forms, and above-mentioned general formula (II) is by R
3R
4R
5SiX, R
6R
7SiX
2Or their mixture (R wherein
3～R
7Identical with X with general formula (II)) hydrolytic condensate form, at least a portion at the organism position of general formula (I) combines with this hydrolytic condensate simultaneously, the structure position (B) of formation general formula (1) is the preferred scheme of the present invention.
In addition, among the present invention, can in the curable resin shown in the general formula (1), cooperate hydrosilylation catalysts or radical initiator or the two, to obtain curable resin composition.In addition, can in this curable resin composition, cooperate the compound of the hydrosilylation that has hydrogen atom at least on 1 Siliciumatom or have the compound of unsaturated group or the two.
Below the present invention is carried out more specific description.
Curable resin of the present invention shown in above-mentioned general formula (1), has the molecular structure that comprises close structural unit (A) and thin structural unit (B), has at least one unsaturated link(age).Wherein, it is 0.68～0.8 metal oxide that close structural unit (A) contains the packing coefficient Kp that is calculated by aforementioned calculation formula (2), the packing coefficient Kp that dredges structural unit (B) less than 0.68, contain organism and organo-metallic oxide compound and constitute.
Close structural unit (A), preferably the metal oxide position that does not comprise the three-dimensional polyhedral structure skeleton of having of organism position by above-mentioned general formula (I) forms.Wherein, so-called organism position is meant among the R (organic radical) in the general formula (I), with atoms metal (being Si and M) bonded position.In the general formula (I), at least 1 of preferred R is the organic radical with the unsaturated group shown in the above-mentioned formula (a)～(c).Should illustrate that a plurality of R of general formula (I) can be all different.
General formula (I) is the cage modle silicone resin that is made of three-dimensional polyhedral structure skeleton and R, as the one example, with the w in the general formula (I) is 8, x, y and z are 0 o'clock, w is 10, x, y and z are that 0 o'clock and w are 12, and x, y and z are that 0 o'clock the particular instantiation of structure is in following structural formula (3), (4) and (5).But the structural unit shown in the general formula (I) is not limited to the structure shown in this structural formula (3), (4) and (5).Should illustrate that these structures are known,, illustrate by the parsing of X ray crystalline texture for the structure of specific functional group.
Above-mentioned general formula (I) can be by making RSiX in the presence of acid or alkaline catalysts
3Or MX
4Being hydrolyzed more than a kind of shown compound obtains with condensation reaction.At this, R, X have the implication identical with M with R, the X of general formula (I) with M.Wherein, the preferably above-mentioned (a) and (b) of the part of R or (c) unsaturated group of expression.If the concrete example of the preferred unsaturated group of illustration can be enumerated 3-methacryloxypropyl, 3-acryloxy propyl group, aryl, vinyl and styryl.In addition, X is the hydrolization group of halogen atom, alkoxyl group, if concrete example is shown, can enumerate chlorine, bromine, methoxyl group, oxyethyl group, positive propoxy and isopropoxy.
If RSiX is shown
3The preference of shown compound can be enumerated trichlorosilane, METHYL TRICHLORO SILANE, ethyl trichlorosilane, the sec.-propyl trichlorosilane, butyl trichlorosilane, tertiary butyl trichlorosilane, the cyclohexyl trichlorosilane, phenyl-trichloro-silicane, vinyl trichloro silane, allyltrichlorosilane, the styryl trichlorosilane, the cyclohexenyl trichlorosilane, Trimethoxy silane, methyltrimethoxy silane, ethyl trimethoxy silane, the sec.-propyl Trimethoxy silane, butyl trimethoxy silane, tert-butyl trimethoxy silane, cyclohexyl trimethoxy silane, phenyltrimethoxysila,e, vinyltrimethoxy silane, allyltrimethoxysilanis, the styryl Trimethoxy silane, the cyclohexenyl Trimethoxy silane, triethoxyl silane, Union carbide A-162, ethyl triethoxysilane, the sec.-propyl triethoxyl silane, the butyl triethoxyl silane, tertiary butyl triethoxyl silane, the cyclohexyl triethoxyl silane, phenyl triethoxysilane, vinyltriethoxysilane, allyltriethoxysilane, the styryl triethoxyl silane, the cyclohexenyl triethoxyl silane, tripropoxy silane, methyl tripropoxy silane, ethyl tripropoxy silane, sec.-propyl tripropoxy silane, butyl tripropoxy silane, tertiary butyl tripropoxy silane, cyclohexyl tripropoxy silane, phenyl tripropoxy silane, vinyl tripropoxy silane, allyl group tripropoxy silane, styryl tripropoxy silane, cyclohexenyl tripropoxy silane, the methacryloxy Union carbide A-162, the methacryloxy methyltrimethoxy silane, 3-methacryloxypropyl trichlorosilane, the 3-methacryloxypropyl trimethoxy silane, 3-methacryloxypropyl triethoxyl silane, 3-acryloxy propyl trimethoxy silicane, 3-acryloxy propyltrichlorosilan etc.
In addition, M is silicon, germanium, titanium or zirconium.At this, if MX is shown
4Shown in the preference of compound, can enumerate tetrachloro silicane, tetramethoxy-silicane, tetraethoxysilane, tetrachloro germane, tetramethoxy germane, tetraethoxy germane, ethanolato-titanium, titanium propanolate, titanium isopropoxide, titanium butoxide, isobutoxy titanium, oxyethyl group zirconium, propoxy-zirconium, isopropoxy zirconium, butoxy zirconium, isobutoxy zirconium etc.
Secondly, dredging structural unit (B) comprises shown in the above-mentioned general formula (I) in the structural unit as the organism position (or substituting group) of the residue that does not comprise three-dimensional polyhedral structure skeleton and has the unitary organo-metallic oxide compound of the chain shown in the above-mentioned general formula (II) (silicoorganic compound).In other words, comprise the position of from the structural unit shown in the above-mentioned general formula (I), having removed close structure position (A) and the structural unit shown in the general formula (II).More particularly, as following illustration, preferably by R
3R
4R
5SiX, R
6R
7SiX
2Or their mixture (R wherein
3～R
7Identical with X with general formula (II)) the chain-like structure thing of organo-metallic oxide compound of the general formula (II) that forms of hydrolytic condensate and the organism position of general formula (I) [promptly, removed the residue (or substituting group) of three-dimensional polyhedral structure skeleton shown in the general formula (I) in the structural unit] or at least a portion combination of X, form the structure position (B) of general formula (1).That is, the part at the organism position of general formula (1) can combine with general formula (II), and the whole of the organism position of general formula (1) can combine with general formula (II).To draw in the chain unit of general formula (II) with the organism position of general formula (II) bonded general formula (I).
Structural unit shown in the above-mentioned general formula (II) can be by making R in the presence of acid or alkaline catalysts
3R
4R
5SiX or R
6R
7SiX
2Shown in being hydrolyzed more than a kind and condensation reaction and obtaining of compound.At this, R
3～R
7R with general formula (II)
3～R
7Implication is identical.R
3～R
7A part when being unsaturated group, if preferred concrete example is shown, can enumerate 3-methacryloxypropyl, 3-acryloxy propyl group, aryl, vinyl and styryl.X is halogen atom or alkoxyl group, if concrete example is shown, can enumerate chlorine, bromine, methoxyl group, oxyethyl group, positive propoxy and isopropoxy.
If R is shown
3R
4R
5The preference of the compound shown in the SiX can be enumerated trimethylchlorosilane, vinyl-dimethyl base chlorosilane, dimethylchlorosilane, the phenyl dimethylchlorosilane, phenyl chlorosilane, chlorotriethyl silane, the trivinyl chlorosilane, methyl divinyl chlorosilane, allyldimethylcholrosilane, 3-methacryloxypropyl dimethylchlorosilane, 3-acryloxy propyl-dimethyl chlorosilane, the styryl dimethylchlorosilane, the trimethylammonium methoxy silane, the vinyl-dimethyl methoxylsilane, the dimethyl methyl TMOS, phenyl dimethyl methyl TMOS, the phenyl methoxy silane, the triethyl methoxy silane, the trivinyl methoxy silane, methyl divinyl methoxy silane, the allyl dimethyl methoxylsilane, 3-methacryloxypropyl dimethyl methyl TMOS, 3-acryloxy propyl-dimethyl methoxy silane, styryl dimethyl methyl TMOS, trimethylethoxysilane, vinyl-dimethyl base oxethyl silane, dimethylethoxysilane, the phenyl dimethylethoxysilane, phenyl ethoxy silane, triethyl-ethoxy-silicane alkane, the trivinyl Ethoxysilane, methyl divinyl Ethoxysilane, allyl dimethyl base oxethyl silane, 3-methacryloxypropyl dimethylethoxysilane, 3-acryloxy propyl-dimethyl Ethoxysilane, the styryl dimethylethoxysilane, trimethylammonium propoxy-silane, vinyl-dimethyl base propoxy-silane, the dimethyl propylene TMOS, phenyl dimethyl propylene TMOS, phenyl propoxy-silane, triethyl propoxy-silane, trivinyl propoxy-silane, methyl divinyl propoxy-silane, allyl dimethyl base propoxy-silane, 3-methacryloxypropyl dimethyl propylene TMOS, 3-acryloxy propyl-dimethyl propoxy-silane, styryl dimethyl propylene TMOS, trimethylammonium isopropoxy silane, vinyl-dimethyl base isopropoxy silane, dimethyl isopropoxy silane, phenyl dimethyl isopropoxy silane, the propyloxy phenyl TMOS, triethyl isopropoxy silane, trivinyl isopropoxy silane, methyl divinyl isopropoxy silane, allyl dimethyl base isopropoxy silane, 3-methacryloxypropyl dimethyl isopropoxy silane, 3-acryloxy propyl-dimethyl isopropoxy silane, styryl dimethyl isopropoxy silane etc.
In addition, if R is shown
6R
7SiX
2The preference of shown compound can be enumerated dimethyldichlorosilane(DMCS), the vinyl dimethyl dichlorosilane (DMCS), the divinyl dichlorosilane, the allyl methyl dichlorosilane, dimethyl dichlorosilane (DMCS), dichloromethyl phenylsilane, the methylethyl dichlorosilane, the ethyl vinyl dichlorosilane, the allyl ethyl dichlorosilane, the styryl dimethyl dichlorosilane (DMCS), the styryl ethyl dichlorosilane, 3-methacryloxypropyl dimethyl dichlorosilane (DMCS), dimethyldimethoxysil,ne, the vinyl methyl dimethoxysilane, divinyl dimethoxy silane, allyl methyl dimethoxy silane, methyl dimethoxysilane, aminomethyl phenyl dimethoxy silane, methylethyl dimethoxy silane, ethyl vinyl dimethoxy silane, allyl ethyl dimethoxy silane, the styryl methyl dimethoxysilane, styryl ethyl dimethoxy silane, 3-methacryloxypropyl methyl dimethoxysilane, dimethyldiethoxysilane, the vinyl methyldiethoxysilane, the divinyl diethoxy silane, the allyl methyl diethoxy silane, methyldiethoxysilane, the aminomethyl phenyl diethoxy silane, the methylethyl diethoxy silane, the ethyl vinyl diethoxy silane, the allyl ethyl diethoxy silane, the styryl methyldiethoxysilane, styryl ethyl diethoxy silane, 3-methacryloxypropyl methyldiethoxysilane, dimethyl dipropoxy silane, vinyl methyl dipropoxy silane, divinyl dipropoxy silane, allyl methyl dipropoxy silane, methyl dipropoxy silane, aminomethyl phenyl dipropoxy silane, methylethyl dipropoxy silane, ethyl vinyl dipropoxy silane, allyl ethyl dipropoxy silane, styryl methyl dipropoxy silane, styryl ethyl dipropoxy silane, 3-methacryloxypropyl methyl dipropoxy silane, dimethyl diisopropoxy silane, vinyl methyl diisopropoxy silane, divinyl diisopropoxy silane, allyl methyl diisopropoxy silane, methyl diisopropoxy silane, aminomethyl phenyl diisopropoxy silane, methylethyl diisopropoxy silane, ethyl vinyl diisopropoxy silane, allyl ethyl diisopropoxy silane, styryl methyl diisopropoxy silane, styryl ethyl diisopropoxy silane, 3-methacryloxypropyl methyl diisopropoxy silane etc.
Curable resin of the present invention, can obtain by making the reactive organic silicon compound shown in cage modle silicone resin shown in the above-mentioned general formula (I) and the general formula (II), the unsaturated link(age) that the curable resin that obtains has a structural unit shown in above-mentioned general formula (I) and the above-mentioned general formula (II) is by crosslinked or hydrolytic condensation and the molecular structure of condensation.In addition, it is 0.68～0.8 close structural unit (A) and packing coefficient less than 0.68 thin structural unit (B) that this curable resin has the packing coefficient that is calculated by free body integration rate, and has at least 1 unsaturated link(age).
Use the calculating of packing coefficient Kp to calculate among the present invention by following calculating formula (2).
Kp＝An·Vw·p/Mw (2)
(wherein, An=N, Vw=Van der waals volumes, p=density, Mw=molecular weight), wherein
Vw＝∑Va
Va＝4π/R
3-∑1/3πhi
2(3Ra-hi)
hi＝R-(R
2+di
2-Ri
2)/2di
(wherein, the R=atomic radius, Ri=is in conjunction with atomic radius and d=interatomic distance).
In the calculating of above-mentioned packing coefficient, atomic radius and interatomic distance have used the Japanization association chemical brief guide of work basis to compile the numerical value of ordering record in 3 editions.That is,, use for atomic radius
Interatomic distance has used
For example, the density of the glass shown in M=Siliciumatom, w=0, x=2, y=0 and the z=0 of general formula (I) is 2.23g/cm
3, its packing coefficient is 0.747.The R of general formula (I) is that the density of prestox silicious sesquioxane of the formation cube structure of methyl, w=8, x=0, y=0 and z=0 is 1.49g/cm
3, packing coefficient is 0.697.In addition, the R of general formula (II)
6And R
7For the density of the octamethylcyclotetrasiloxane of the formation ring texture of methyl, j=0, k=4 and l=0 is 0.956g/cm
3, its packing coefficient is 0.576.Similarly, R
3And R
4, R
5, R
6And R
7For the density of the octamethyltrisiloxane of the formation chain-like structure of methyl, j=2, k=1 and l=0 is 0.820g/cm
3, its packing coefficient is 0.521.That is, the packing coefficient with metal oxide of the three-dimensional polyhedral structure of Siliciumatom and the Sauerstoffatom bonded more than 3 is more than 0.69, becomes the close structural unit among the present invention.In addition, the packing coefficient that forms the compound of ring-type and chain-like structure is 0.576 and 0.521, becomes the thin structural unit among the present invention.
In addition, curable resin of the present invention, the structural unit weight ratio (A)/(B) of close structural unit (A) and thin structural unit (B) is 0.01～5.00, is preferably 0.5～3.00.(A)/(B) less than 0.01 o'clock, close structure was very few, and the mechanical properties and the thermotolerance of the formed body that the curable resin forming and hardening is obtained significantly worsen.In addition, 5.00 when above, and the thin structure position of giving the formed body flexibility is very few, and toughness significantly worsens and becomes fragile.
In addition, curable resin of the present invention, molecular-weight average are 800～60000.If molecular-weight average less than 800, becomes fragile after the moulding easily, if opposite to 60000, the difficulty that becomes when curing molding is processed with is made troubles to processing.Should illustrate that molecular-weight average can adopt known GPC determinator to measure.
As RSiX
3Or MX
4Shown compound and R
3R
4R
5SiX or R
6R
7SiX
2Shown in the acid catalyst that uses in the hydrolysis of compound and the condensation, can enumerate hydrochloric acid and sulfuric acid.In addition, also they can be mixed and use, when hydrolization group is halogen atom, the hydrogen halide that generates in the time of also can utilizing hydrolysis.
As the basic catalyst that uses in hydrolysis and the condensation, can enumerate alkali metal hydroxides such as potassium hydroxide, sodium hydroxide, cesium hydroxide, perhaps ammonium hydroxide salt such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, hydroxide benzyltrimethylammon.um, hydroxide benzyl triethyl ammonium ammonium.Wherein, from the high aspect of catalytic activity, preferably use tetramethylammonium hydroxide.Basic catalyst uses as the aqueous solution usually.
Must there be water in hydrolysis reaction, but can supply with water by the aqueous solution of catalyzer, also can add with the form of water in addition.The water yield is to be enough to make more than the amount of hydrolization group hydrolysis, is preferably 1.0～1.5 times of amounts of theoretical amount.
Among the present invention, can in curable resin, cooperate hydrosilylation catalysts or radical initiator, perhaps cooperate both and obtain curable resin composition.In addition,, carry out hydrosilylation or radical polymerization, can access cured article (formed body) by making this curable resin composition thermofixation or photocuring.In addition, except hydrosilylation catalysts or radical initiator, also can further cooperate to have the compound of unsaturated group in the compound that has hydrogen atom on the Siliciumatom, the molecule and obtain curable resin composition.Promptly,, curable resin obtains the purpose of formed body from being solidified, perhaps improving the purpose of the rerum natura etc. of the formed body obtain sets out, cooperate hydrosilylation catalysts, thermal polymerization, thermopolymerization promotor, photopolymerization promoter, light-initiated auxiliary agent, sensitive agent etc. as the additive that promotes reaction, obtain curable resin composition.
In the curable resin composition, having the compound of hydrogen atom on the Siliciumatom that curable resin uses, is oligopolymer and the monomer that has hydrogen atom in the molecule at least on the Siliciumatom of the hydrosilylation more than 1.Wherein, as the oligopolymer that has hydrogen atom on the Siliciumatom, can enumerate poly-hydrogen radical siloxane class, polydimethyl hydrogen base siloxy siloxane class and multipolymer thereof, the terminal siloxanes of modifying with dimethyl hydrogen base siloxy-.In addition, as the monomer that has hydrogen atom on the Siliciumatom, can enumerate annular siloxane classes such as tetramethyl-ring tetrasiloxane, pentamethyl-D5, dihydro sily oxide class, three hydrogen silicomethane classes, dihydro silicomethane class, single hydrogen silicomethane class, dimethylsilane oxygen radical siloxane class etc. can be with mixing more than 2 kinds in them.
In addition, in the curable resin composition, for the compound that uses with curable resin, roughly be divided into reactive oligomers and lower molecular weight and low viscous reactive monomer that it is about 2～20 polymkeric substance for the repeat number of structural unit with unsaturated group.In addition, also roughly be divided into simple function unsaturated compound with 1 unsaturated group and multifunctional unsaturated compound with 2 above unsaturated groups.
Wherein, as reactive oligomers, can enumerate polyvinyl siloxane class, polydimethyl vinyl siloxy siloxane class and multipolymer thereof, terminal type siloxane, epoxy acrylate, epoxidized oil acrylate, urethane acrylate, unsaturated polyester, polyester acrylate, polyether acrylate, vinyl acrylate, polyenoid/mercaptan, organic silicon acrylic ester, polyhutadiene, polymethyl acrylic acid styryl ethyl ester etc. with the dimethylvinylsiloxy modification.Simple function unsaturated compound and multifunctional unsaturated compound are arranged in these.
As reactive monofunctional monomer, can enumerate vinyl substituted silicon compound classes such as triethyl vinyl silanes, triphenyl vinyl silanes, cyclic olefins such as tetrahydrobenzene, vinylbenzene, vinyl acetate, N-vinyl pyrrolidone, butyl acrylate, 2-EHA, the just own ester of vinylformic acid, cyclohexyl acrylate, vinylformic acid ester in the positive last of the ten Heavenly stems, isobornyl acrylate, vinylformic acid two cyclopentenes oxygen base ethyl esters, vinylformic acid phenoxy ethyl, trifluoroethyl methacrylate etc.
As reactive polyfunctional monomer, can enumerate tetrem thiazolinyl silane, vinyl substituted silicon compounds such as divinyl tetramethyl disiloxane, tetramethyl-tetrem thiazolinyl cyclotetrasiloxane, vinyl substituted ring-type silicon compounds such as pentamethyl-five vinyl D5s, two (trimethyl silyl) acetylene, acetylene-derivatives such as dibenzenyl, norbornadiene, Dicyclopentadiene (DCPD), ring-type polyenoid classes such as cyclooctadiene, vinyl substituted cyclic olefins such as vinyl cyclohexene, the Vinylstyrene class, the diacetylene-benzene class, the TriMethylolPropane(TMP) diallyl ether, tetramethylolmethane three allyl ethers, tripropylene glycol diacrylate, 1,6 hexanediol diacrylate, the bisphenol A diglycidyl ether diacrylate, Viscoat 335HP, the hydroxy new pentane acid neopentylglycol diacrylate, Viscoat 295, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, dipentaerythritol acrylate etc.
As the compound that has unsaturated group in the molecule, except above illustrative compound, can use various reactive oligomers, monomer.In addition, these reactive oligomers, monomer can be used independently, can also be 2 or more kinds in combination.
Have the compound that has unsaturated group in the compound of hydrogen atom and the molecule on the Siliciumatom that uses among the present invention, can be used independently, can also be 2 or more kinds in combination.
As mentioned above, curable resin composition of the present invention obtains by cooperate the compound that contains hydrogen atom on hydrosilylation catalysts, radical initiator or they and the Siliciumatom, the compound with unsaturated group in curable resin.Formed body of the present invention is by obtaining this curable resin composition forming and hardening.That is,, can access cured article by with curable resin composition hydrosilylation cure and radical polymerization.
When cooperating hydrosilylation catalysts, its addition is with respect to the weight of curable resin, in atoms metal, preferably with 1～1000ppm, more preferably add with the scope of 20～500ppm.In addition, when cooperating Photoepolymerizationinitiater initiater or thermal polymerization as radical initiator, its addition is preferably the scope of 0.1～5 weight part, more preferably the scope of 0.1～3 weight part with respect to curable resin 100 weight parts.If this addition less than 0.1 weight part, curing becomes insufficient, and the intensity of the sealing material that obtains, rigidity reduce.On the other hand, if surpass 5 weight parts, might produce the problem such as painted of sealing material.In addition, can use hydrosilylation catalysts and radical initiator separately, also can will also use more than 2 kinds.
As hydrosilylation catalysts, can enumerate platinum chloride, Platinic chloride, the complex compound of Platinic chloride and alcohol, aldehyde, ketone, the complex compound of Platinic chloride and olefines, platinum metals series catalysts such as the complex compound of platinum and vinylsiloxane, dicarbapentaborane dichloro platinum and palladium series catalyst, rhodium series catalysts.Wherein, from the catalytic activity aspect, the complex compound of complex compound, platinum and the vinylsiloxane of preferred Platinic chloride, Platinic chloride and olefines.In addition, can use them separately, also can will also use more than 2 kinds.
The Photoepolymerizationinitiater initiater that uses when making curable resin composition become Photocurable resin composition is fit to use compounds such as methyl phenyl ketone system, bitter almond oil camphor system, benzophenone series, thioxanthone system, acylphosphine oxide system.Can enumerate Trichloroacetophenon, diethoxy acetophenone, 1-phenyl-2-hydroxy-2-methyl propane-1-ketone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholino propane-1-ketone, benzoin methylether, benzyl dimethyl ketal, benzophenone, thioxanthone, 2 particularly; 4,6-trimethylbenzoyl diphenyl phosphine oxide, aminomethyl phenyl glyoxylic ester, camphorquinone, benzil, anthraquinone, Michler's keton etc.In addition, also can will also use with light-initiated auxiliary agent, the sensitive agent of Photoepolymerizationinitiater initiater combination performance effect.
As the thermal polymerization that uses in the above purpose, be fit to use various organo-peroxides such as ketone peroxide system, peroxy ketal system, hydroperoxidation system, dialkyl peroxide system, diacyl peroxide system, peroxy dicarbonate system, peroxyester system.Can enumerate cyclohexanone peroxide, 1 particularly, two (peroxidation of the uncle's hexyl) pimelinketone of 1-, cumene hydroperoxide, dicumyl peroxide, benzoyl peroxide, peroxidation di-isopropyl, tert-butyl hydroperoxide-2-ethylhexanoate etc., but be not limited to these.In addition, these thermal polymerizations may be used alone, can also be 2 or more kinds in combination.
In the scope that does not break away from the object of the invention, can in curable resin composition, add various additives.As various additives, can enumerate organic/inorganic filler, softening agent, fire retardant, thermo-stabilizer, antioxidant, photostabilizer, UV light absorber, lubricant, static inhibitor, releasing agent, whipping agent, nuclear agent, tinting material, linking agent, dispersing auxiliary, resinous principle etc.
The formed body that is formed by curable resin of the present invention can solidify by any one and boths' that utilize heating or rayed to make to contain hydrosilylation catalysts, radical polymerization initiator curable resin composition and make.When making multipolymer (formed body) by heating, its mold temperature is according to the selection of thermal polymerization and promotor, can select from the wide region about room temperature to 200 ℃.In this case, by making its polymerizing curable in mould or on the steel band, can access the silicone resin formed body of desired shape.More particularly, can use injection molding, extrusion moulding, compressed moulding, transfer molding, calendering formation, these common whole method for processing forming of casting (casting) moulding.
In addition, when making multipolymer (formed body),, can access formed body by the ultraviolet ray of illumination wavelength 100～400nm or the visible light of wavelength 400～700nm by rayed.There is no particular restriction for the light wavelength of using, and especially preferably uses the near-ultraviolet ray of wavelength 200～400nm.As the lamp in ultraviolet generation source, can enumerate Cooper-Hewitt lamp (output rating: 0.4～4W/cm), high pressure mercury vapour lamp (40～160W/cm), extra-high-pressure mercury vapour lamp (173～435W/cm), metal halide lamp (80～160W/cm), xenon flash lamp (80～120W/cm), electrodeless discharge lamp (80～120W/cm) etc.These UV-lamp have feature because beam split separately distributes, and therefore select according to the kind of the light trigger that uses.
As the method that obtains silicone resin multipolymer (formed body) by rayed, for example can enumerate and to inject in the mould that has the arbitrary mould cavity shape and constitute by transparent materials such as silica glasss, carry out polymerizing curable with above-mentioned UV-lamp irradiation ultraviolet radiation, from mould, make its demoulding, thereby make the method for the formed body of desired shape; When not using mould, the spreader that for example uses scraper or roller shape is coating curable resin composition of the present invention on the steel band that moves, and makes its polymerizing curable with above-mentioned UV-lamp, thereby makes the method etc. of flaky formed body.In addition, also the method that adopts heating and rayed to obtain formed body can be used in combination among the present invention.
The effect of invention
Adopt curable resin of the present invention, can access and have the such high tenacity of the such intensity of unorganic glass, the transparency, thermotolerance and dimensional stability and plastics and the formed body of processibility simultaneously, can be at for example optical applications of lens, CD, optical fiber and flat display substrate etc., various conveying machineries use in the various uses such as the window material of dwelling house etc.In addition, the formed body that obtains is the transparent component of lightweight and high impact, and it utilizes scope to become extensively as the glass equivalent material, and the utility value on the industry is also high.
Embodiment
Embodiments of the invention below are shown.
Embodiment 1
In 4 mouthfuls of flasks of the 2L that possesses agitator and dropping funnel, pack into Virahol 300mL and toluene 600mL, 20w% tetramethylammonium hydroxide aqueous solution 22.37g (tetramethylammonium hydroxide 4.55g/0.05mol, water 17.82g/0.99mol).With the mixing solutions of vinyltrimethoxy silane 44.4g/0.30mol and the Virahol 50mL dropping funnel of packing into, limit stirring reaction container, the limit at room temperature dripped with 3 hours.Dripping the end back stirred 3 hours under situation about not heating.Stir after 3 hours, stop to stir, at room temperature made the reaction soln slaking 18 hours.This reaction soln joined among the 0.1M aqueous citric acid solution 1L neutralize, water is washed after becoming neutrality again, adds anhydrous magnesium sulfate and dewaters.After the anhydrous magnesium sulfate filtering separation, under reduced pressure concentrate.With the tetrahydrofuran (THF) 200mL dissolving enriched material of dehydration, in 4 mouthfuls of flasks of the 1L that possesses agitator and dropping funnel of packing into.In reaction vessel, add the pyridine 100mL of dehydration and in dropping funnel, add dimethyldichlorosilane(DMCS) 3.2g/0.025mol and trimethylchlorosilane 2.7g/0.025mol and tetrahydrofuran (THF) 30mL, stir reaction vessel under nitrogen gas stream on the limit, and the limit at room temperature dripped with 3 hours.Dripping the end back stirred 3 hours under situation about not heating.Stir after 3 hours, behind the adding toluene 300mL, water is washed up to becoming neutrality reaction soln, adds anhydrous magnesium sulfate and dewaters.With the anhydrous magnesium sulfate filtering separation, under reduced pressure concentrate, thereby obtain curable resin [general formula (1)] 27.1g as water white liquid.
In the 1H-NMR of this curable resin,, confirm that the hydrolytic condensate from vinyltrimethoxy silane is a cagelike structure owing to observe the sharp signal of vinyl.Thus, by metal oxide, promptly the close structural unit (A) of the three-dimensional polyhedral structure of Si oxide formation can be assumed to the usefulness (SiO that are made of 8 of Siliciumatoms and 12 of Sauerstoffatoms for conduct
3/2)
8The cube structure of expression, the Kp of derivation is 0.73.In addition, (A) part in addition of above-mentioned curable resin is as (H
2C=CH-SiO
3/2)
8The vinyl of residue and (Me
3SiO
1/2) and (Me
2SiO), be to dredge structure position (B), the weight ratio of being obtained by them [(A)/(B)] is 1.302, the number-average molecular weight Mn that is obtained by GPC is 5200.In addition, dredge structural unit (B) by vinyl, (Me
3SiO
1/2) and (Me
2SiO) form, do not form three-dimensional polyhedral structure, Kp is less than 0.69.Should illustrate, when calculating the Kp of close structural unit (A), because (SiO
3/2)
8Be the part of (A), exist, therefore can not remove, can not directly obtain Kp as the part in general formula (I) resin.Therefore, as minimum and can proximate compound, use (HSiO to the influence of Kp
3/2)
8Calculate.
Embodiment 2
Curable resin 100 weight parts and dicumyl peroxide (the system パ one Network ミ Le D of NOF Corp) 2 weight parts that obtain among the embodiment 1 are mixed up to reaching evenly, make curable resin composition.With its be cast to by in the mould of sheet glass assembling forming thickness 1mm, 100 ℃ of heating 1 hour down,,,, obtain cured article 160 ℃ of heating 1 hour and heated 2 hours down down at 180 ℃ 140 ℃ of heating 1 hour down 120 ℃ of heating 1 hour down.
Embodiment 3
Curable resin 58 weight parts that obtain among the embodiment 1, the terminal poly-methyl hydrogen radical siloxane of modifying with trimethyl silyl (the system HMS-992 of ア ヅ マ Star Network ス Co., Ltd.) 42 weight parts and platinum-vinylsiloxane complex compound (the system SIP6830.3 of ア ヅ マ Star Network ス Co., Ltd.) 0.5 weight part are mixed up to reaching evenly, make curable resin composition.With its be cast to by in the mould of sheet glass assembling forming thickness 1mm, 100 ℃ of heating 1 hour down,,,, obtain cured article 160 ℃ of heating 1 hour and heated 2 hours down down at 180 ℃ 140 ℃ of heating 1 hour down 120 ℃ of heating 1 hour down.
Embodiment 4
Curable resin 58 weight parts that obtain among the embodiment 1, the terminal poly-methyl hydrogen radical siloxane of modifying with trimethyl silyl (the system HMS-992 of ア ヅ マ Star Network ス Co., Ltd.) 21 weight parts, dicumyl peroxide (the system パ one Network ミ Le D of NOF Corp) 2 weight parts and platinum-vinylsiloxane complex compound (the system SIP6830.3 of ア ヅ マ Star Network ス Co., Ltd.) 0.5 weight part are mixed up to reaching evenly, make curable resin composition.With its be cast to by in the mould of sheet glass assembling forming thickness 1mm, 100 ℃ of heating 1 hour down,,,, obtain cured article 160 ℃ of heating 1 hour and heated 2 hours down down at 180 ℃ 140 ℃ of heating 1 hour down 120 ℃ of heating 1 hour down.
[comparative example 1]
Dipentaerythritol acrylate 100 weight parts and dicumyl peroxide (the system パ one Network ミ Le D of NOF Corp) 2 weight parts are mixed up to reaching evenly, make curable resin composition.With its be cast to by in the mould of sheet glass assembling forming thickness 1mm, 100 ℃ of heating 1 hour down,,,, obtain cured article 160 ℃ of heating 1 hour and heated 2 hours down down at 180 ℃ 140 ℃ of heating 1 hour down 120 ℃ of heating 1 hour down.
Use the transmissivity of above-mentioned each cured article that obtains of spectrophotometric determination.With measure wavelength 800,600 and 400nm transmissivity the results are shown in table 1.
[table 1]
Claims (7)
1. the curable resin that has the organo-metallic structure, this curable resin has the molecular structure that comprises close structural unit (A) and thin structural unit (B) shown in the following general formula (1), it is characterized in that: close structural unit (A) is to comprise the structural unit that packing coefficient Kp is 0.68～0.8 metal oxide, this packing coefficient Kp is calculated by free body integration rate and is obtained by following calculating formula (2), dredging structural unit (B) is that above-mentioned packing coefficient Kp is less than 0.68, the structural unit that contains organism and organo-metallic oxide compound and constitute, the weight ratio of structural unit (A)/(B) is 0.01～5.00, and has at least one unsaturated link(age), molecular-weight average is 800～60000
-{(A)-(B)
m}
n- (1)
Wherein, m and n represent the integer more than 1,
Kp＝An·Vw·p/Mw (2)
Wherein, An=N, Vw=Van der waals volumes, p=density, Mw=molecular weight, Vw=∑ Va, Va=4 π/R
3-∑ 1/3 π hi
2(3Ra-hi), hi=Ra-(Ra
2+ di
2-Ri
2)/2di, the Ra=atomic radius, Ri=is in conjunction with atomic radius and di=interatomic distance.
2. the described curable resin of claim 1, wherein, close structural unit (A) comprises the metal oxide position that does not comprise the three-dimensional polyhedral structure skeleton of having of organism position of following general formula (I), dredge structural unit (B) and comprise the chain unit that constitutes by the organo-metallic oxide compound shown in the following general formula (II) and the organism position of general formula (I)
(RSiO
3/2)
w(MO
2)
x(RXSiO)
y(XMO
3/2)
z (I)
(R
3R
4R
5SiO
1/2)
j(R
6R
7SiO)
k{R
6R
7XSiO
1/2}
l (II)
Wherein, R is (a)-R
1-OCO-CR
2=CH
2, (b)-R
1-CR
2=CH
2Or (c)-CH=CH
2Unsaturated group, alkyl, cycloalkyl, cycloalkenyl group, phenyl, hydrogen atom, alkoxyl group or the alkyl siloxy of expression, a plurality of R can differ from one another in the formula (I), but at least 1 comprises above-mentioned (a) and (b) or (c) any, R
1Expression alkylidene group, alkylidene or phenylene, R
2The expression hydrogen or alkyl, in addition, R
3～R
7Be (a)-R
1-OCO-CR
2=CH
2, (b)-R
1-CR
2=CH
2Or (c)-CH=CH
2Unsaturated group, alkyl, cycloalkyl, cycloalkenyl group, phenyl, hydrogen atom, alkoxyl group or the alkyl siloxy of expression, in addition, M is the atoms metal of silicon, germanium, titanium or zirconium, X is halogen atom or alkoxyl group, w is the integer more than 4, x, y and z are the integers that satisfies w+x+y+z 〉=8, and j, k and l represent the integer more than 0 respectively.
3. the described curable resin of claim 2, wherein, general formula (I) is by RSiX
3, MX
4Or the hydrolytic condensate of their mixture forms, and wherein R, M are identical during with general formula (I) with X.
4. the described curable resin of claim 2, wherein, general formula (II) is by R
3R
4R
5SiX, R
6R
7SiX
2Or the formation of the hydrolytic condensate of their mixture, wherein R
3～R
7Identical with general formula (II) with X, the organism position of general formula (I) or at least a portion of X combine with this hydrolytic condensate and form the structure position (B) of general formula (1).
5. curable resin composition, it forms by cooperate hydrosilylation catalysts, radical initiator or both in each described curable resin of claim 1～4.
6. the described curable resin composition of claim 5 wherein also is combined with the compound that has unsaturated group in the compound that has the hydrosilylation of hydrogen atom at least 1 Siliciumatom, the molecule or both.
7. formed body, it is by obtaining claim 5 or 6 described curable resin composition forming and hardenings.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP085491/2006 | 2006-03-27 | ||
| JP2006085491 | 2006-03-27 | ||
| PCT/JP2007/055849 WO2007119477A1 (en) | 2006-03-27 | 2007-03-22 | Curable resin, curable resin compositions and moldings thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101410437A true CN101410437A (en) | 2009-04-15 |
| CN101410437B CN101410437B (en) | 2012-01-04 |
Family
ID=38609261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007800106023A Expired - Fee Related CN101410437B (en) | 2006-03-27 | 2007-03-22 | Curable resin, curable resin compositions and moldings thereof |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP5108751B2 (en) |
| KR (1) | KR101075358B1 (en) |
| CN (1) | CN101410437B (en) |
| TW (1) | TWI411648B (en) |
| WO (1) | WO2007119477A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102627859A (en) * | 2011-01-17 | 2012-08-08 | 信越化学工业株式会社 | A silicone resin composition and an optical semiconductor device making use of the composition |
| CN110387043A (en) * | 2019-07-12 | 2019-10-29 | 湖北大学 | Dendroid organo-silicon compound and preparation method thereof with multiterminal functional group |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006030003A1 (en) * | 2006-05-11 | 2007-11-15 | Wacker Chemie Ag | Silicone resin coating for electronic components |
| JP5234909B2 (en) * | 2007-12-27 | 2013-07-10 | 新日鉄住金化学株式会社 | Alkoxy group-containing cage-type siloxane compound, silanol group-containing cage-type siloxane compound, and methods for producing them |
| KR101504308B1 (en) * | 2007-12-27 | 2015-03-19 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | Curable silicone copolymer containing cage structure and process for production thereof, and curable resin composition comprising curable silicone copolymer containing cage structure and cured product thereof |
| JP5625210B2 (en) * | 2007-12-27 | 2014-11-19 | ナガセケムテックス株式会社 | Curable composition |
| JP5342795B2 (en) * | 2008-03-24 | 2013-11-13 | 新日鉄住金化学株式会社 | 籠 Structure-containing curable silicone copolymer, method for producing the same, curable resin composition using 籠 structure-containing curable silicone copolymer, and cured product thereof |
| JP2010254927A (en) * | 2009-04-28 | 2010-11-11 | Kaneka Corp | Photo-polymerizable composition |
| JP2012097225A (en) * | 2010-11-04 | 2012-05-24 | Daicel Corp | Curable resin composition and cured article |
| CN104387968A (en) * | 2014-12-08 | 2015-03-04 | 江苏诺飞新材料科技有限公司 | Flame retardant coating used for solar panels |
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|---|---|---|---|---|
| EP0348705A3 (en) * | 1988-06-29 | 1991-02-27 | Akademie der Wissenschaften der DDR | Organophilic double-ring silicilic-acid derivatives with cage structures, process for their preparation and their use |
| DE4316101A1 (en) * | 1993-05-13 | 1994-11-17 | Wacker Chemie Gmbh | Organosilicon compounds with a cage-like structure |
| JPH1171462A (en) * | 1997-08-29 | 1999-03-16 | Toshiba Silicone Co Ltd | Novel silicon-containing polymer |
| JP2979145B1 (en) * | 1998-11-18 | 1999-11-15 | 工業技術院長 | New silsesquioxane-containing polymer and method for producing the same |
| JP2000265066A (en) * | 1999-03-17 | 2000-09-26 | Dow Corning Asia Ltd | Organic-solvent-soluble hydrogenated octasilsesquioxane /vinyl group-containing copolymer and insulation material comprising the same |
| JP2000265065A (en) * | 1999-03-17 | 2000-09-26 | Dow Corning Asia Ltd | Production of organic-solvent-soluble hydrogenated octasilsesquioxane/vinyl group-containing copolymer |
| US6252030B1 (en) * | 1999-03-17 | 2001-06-26 | Dow Corning Asia, Ltd. | Hydrogenated octasilsesquioxane-vinyl group-containing copolymer and method for manufacture |
| JP2002363414A (en) * | 2001-06-12 | 2002-12-18 | Asahi Kasei Corp | Basket-like silsesquioxane-containing composition |
| JP4381636B2 (en) * | 2001-11-05 | 2009-12-09 | 新日鐵化学株式会社 | Silicone resin composition and silicone resin molded article |
| JP4142385B2 (en) * | 2002-10-03 | 2008-09-03 | 新日鐵化学株式会社 | Silicone resin composition and silicone resin molded article |
| JP2005290352A (en) * | 2004-03-12 | 2005-10-20 | Asahi Kasei Corp | Compound having basket-shaped silsesquioxane structure |
| JP4742216B2 (en) * | 2004-07-08 | 2011-08-10 | Ｊｎｃ株式会社 | Silicon compounds |
| JP2006265514A (en) * | 2005-02-25 | 2006-10-05 | Asahi Kasei Corp | Copolymer and manufacturing method thereof |
-
2007
- 2007-03-20 TW TW096109534A patent/TWI411648B/en not_active IP Right Cessation
- 2007-03-22 WO PCT/JP2007/055849 patent/WO2007119477A1/en active Search and Examination
- 2007-03-22 JP JP2008510838A patent/JP5108751B2/en not_active Expired - Fee Related
- 2007-03-22 CN CN2007800106023A patent/CN101410437B/en not_active Expired - Fee Related
- 2007-03-22 KR KR1020087025988A patent/KR101075358B1/en active IP Right Grant
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102627859A (en) * | 2011-01-17 | 2012-08-08 | 信越化学工业株式会社 | A silicone resin composition and an optical semiconductor device making use of the composition |
| CN102627859B (en) * | 2011-01-17 | 2015-09-09 | 信越化学工业株式会社 | Organosilicon resin composition and the optical semiconductor device prepared by said composition |
| CN110387043A (en) * | 2019-07-12 | 2019-10-29 | 湖北大学 | Dendroid organo-silicon compound and preparation method thereof with multiterminal functional group |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080108307A (en) | 2008-12-12 |
| TWI411648B (en) | 2013-10-11 |
| JP5108751B2 (en) | 2012-12-26 |
| KR101075358B1 (en) | 2011-10-19 |
| TW200801121A (en) | 2008-01-01 |
| WO2007119477A1 (en) | 2007-10-25 |
| JPWO2007119477A1 (en) | 2009-08-27 |
| CN101410437B (en) | 2012-01-04 |
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