TWI362397B - - Google Patents

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Publication number: TWI362397B
Authority: TW; Taiwan
Prior art keywords: group; hydrogen atom; carbon atoms; general formula; alkyl group
Prior art date: 2006-08-15

Application number

TW096130023A

Other languages

English (en)

Chinese (zh)

Other versions

TW200815492A (en

Inventor

Nobutoshi Sasaki

Toshio Fujita

Hiroshi Uchida

Original Assignee

Showa Denko Kk

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

2006-08-15

Filing date

2007-08-14

Publication date

2012-04-21

2007-08-14 Application filed by Showa Denko Kk filed Critical Showa Denko Kk

2008-04-01 Publication of TW200815492A publication Critical patent/TW200815492A/zh

2012-04-21 Application granted granted Critical

2012-04-21 Publication of TWI362397B publication Critical patent/TWI362397B/zh

Links

125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
150000001875 compounds Chemical class 0.000 claims description 58
239000004593 Epoxy Substances 0.000 claims description 52
125000004432 carbon atom Chemical group C* 0.000 claims description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 43
-1 anthracene compound Chemical class 0.000 claims description 29
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
229910052799 carbon Inorganic materials 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 1
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 1
229910052786 argon Inorganic materials 0.000 claims 1
150000001622 bismuth compounds Chemical class 0.000 claims 1
150000002118 epoxides Chemical class 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 14
238000010992 reflux Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
238000005133 29Si NMR spectroscopy Methods 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
239000000463 material Substances 0.000 description 8
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
238000004821 distillation Methods 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
239000002994 raw material Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
238000007259 addition reaction Methods 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
238000005266 casting Methods 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000002131 composite material Substances 0.000 description 4
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
125000003700 epoxy group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
239000002648 laminated material Substances 0.000 description 3
LUJYQXSLRPMWPJ-UHFFFAOYSA-N n,n,2,2-tetramethylpropanimidamide Chemical compound CN(C)C(=N)C(C)(C)C LUJYQXSLRPMWPJ-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000003566 sealing material Substances 0.000 description 3
238000001179 sorption measurement Methods 0.000 description 3
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical group CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000007809 chemical reaction catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000004927 clay Substances 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical group CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
239000012778 molding material Substances 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
238000007151 ring opening polymerisation reaction Methods 0.000 description 2
239000004576 sand Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 2
239000001648 tannin Substances 0.000 description 2
235000018553 tannin Nutrition 0.000 description 2
229920001864 tannin Polymers 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
239000008096 xylene Substances 0.000 description 2
AGGJWJFEEKIYOF-UHFFFAOYSA-N 1,1,1-triethoxydecane Chemical compound CCCCCCCCCC(OCC)(OCC)OCC AGGJWJFEEKIYOF-UHFFFAOYSA-N 0.000 description 1
BQHZEMZBNIKLKD-UHFFFAOYSA-N 1,2-dimethoxy-1-methylhydrazine Chemical compound CONN(C)OC BQHZEMZBNIKLKD-UHFFFAOYSA-N 0.000 description 1
YNICHAOCDICNOT-UHFFFAOYSA-N 2,2-dimethoxyundecane Chemical compound CCCCCCCCCC(C)(OC)OC YNICHAOCDICNOT-UHFFFAOYSA-N 0.000 description 1
OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
206010020850 Hyperthyroidism Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
239000006087 Silane Coupling Agent Substances 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000012267 brine Substances 0.000 description 1
PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
VANPZBANAIIRJW-UHFFFAOYSA-N diuranium Chemical compound [U]#[U] VANPZBANAIIRJW-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000005611 electricity Effects 0.000 description 1
239000012776 electronic material Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
238000010544 hydroalkylation process reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
150000004060 quinone imines Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
150000003303 ruthenium Chemical class 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
150000003304 ruthenium compounds Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/934—Powdered coating composition

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Compounds (AREA)
Epoxy Resins (AREA)

TW096130023A 2006-08-15 2007-08-14 Novel epoxy compound and process for production thereof TW200815492A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2006221648		2006-08-15

Publications (2)

Publication Number	Publication Date
TW200815492A TW200815492A (en)	2008-04-01
TWI362397B true TWI362397B (2)	2012-04-21

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TW096130023A TW200815492A (en)	2006-08-15	2007-08-14	Novel epoxy compound and process for production thereof

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US (1)	US7880018B2 (2)
EP (1)	EP2055708B1 (2)
JP (1)	JP5153635B2 (2)
KR (1)	KR101013394B1 (2)
CN (1)	CN101501047B (2)
TW (1)	TW200815492A (2)
WO (1)	WO2008020637A1 (2)

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JP5266248B2 (ja) *	2007-11-07	2013-08-21	昭和電工株式会社	エポキシ基含有オルガノシロキサン化合物
EP2270020B1 (en) *	2008-03-24	2014-03-19	Showa Denko K.K.	Epoxy compound and process for producing the epoxy compound
JP5210122B2 (ja) *	2008-10-31	2013-06-12	昭和電工株式会社	接着剤用硬化性組成物
JP5149126B2 (ja) *	2008-11-07	2013-02-20	昭和電工株式会社	半導体封止用硬化性組成物
US8957136B2 (en) *	2010-08-11	2015-02-17	Showa Denko K.K.	Epoxysilicone condensate, curable composition comprising condensate, and cured product thereof
US20160032148A1 (en) *	2013-03-15	2016-02-04	Dow Corning Corporation	A method for making an optical assembly comprising depositing a solid silicone-containing hot melt composition in powder form and forming an encapsulant thereof
CN105669738A (zh) *	2016-01-19	2016-06-15	南昌大学	一种改性硅烷偶联剂的制备方法
JPWO2023008493A1 (2) *	2021-07-29	2023-02-02
CN119798304B (zh) *	2024-12-31	2025-10-10	苏州高泰电子技术股份有限公司	一种耐高温硅烷偶联剂及其制备方法和应用

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JPS5580430A (en)	1978-12-13	1980-06-17	Teijin Ltd	Preparation of polyester
JPS58222160A (ja) *	1982-06-16	1983-12-23	Tokuyama Soda Co Ltd	コ−テイング用組成物
US5206328A (en) *	1990-02-08	1993-04-27	Shin-Etsu Chemical Co., Ltd.	Process for the production of an organopolysiloxane
JPH03255130A (ja)	1990-03-05	1991-11-14	Shin Etsu Chem Co Ltd	エポキシ基含有オルガノポリシロキサンの製造方法
US6080872A (en) *	1997-12-16	2000-06-27	Lonza S.P.A.	Cycloaliphatic epoxy compounds
WO2003084928A1 (en) *	2002-04-08	2003-10-16	Ranbaxy Laboratories Limited	Alpha, omega-dicarboximide derivatives as useful uro-selective α1α adrenoceptor blockers
US7244473B2 (en) *	2003-04-22	2007-07-17	Konica Minolta Medical & Graphic, Inc.	Active ray curable ink-jet composition, image forming method using the same, ink-jet recording apparatus, and triarylsulfonium salt compound
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CN100569209C (zh) *	2004-07-14	2009-12-16	3M创新有限公司	包括环氧乙烷单体的牙科组合物

2007
- 2007-08-13 KR KR1020097001894A patent/KR101013394B1/ko not_active Expired - Fee Related
- 2007-08-13 WO PCT/JP2007/066061 patent/WO2008020637A1/ja not_active Ceased
- 2007-08-13 US US12/377,055 patent/US7880018B2/en not_active Expired - Fee Related
- 2007-08-13 JP JP2008529895A patent/JP5153635B2/ja not_active Expired - Fee Related
- 2007-08-13 CN CN2007800302866A patent/CN101501047B/zh not_active Expired - Fee Related
- 2007-08-13 EP EP07792677.2A patent/EP2055708B1/en not_active Not-in-force
- 2007-08-14 TW TW096130023A patent/TW200815492A/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN101501047B (zh)	2011-12-14
KR101013394B1 (ko)	2011-02-14
US7880018B2 (en)	2011-02-01
EP2055708A1 (en)	2009-05-06
JP5153635B2 (ja)	2013-02-27
EP2055708A4 (en)	2011-01-26
US20100197936A1 (en)	2010-08-05
JPWO2008020637A1 (ja)	2010-01-07
TW200815492A (en)	2008-04-01
KR20090024827A (ko)	2009-03-09
CN101501047A (zh)	2009-08-05
EP2055708B1 (en)	2013-07-17
WO2008020637A1 (en)	2008-02-21

Legal Events

Date	Code	Title	Description
2015-01-21	MM4A	Annulment or lapse of patent due to non-payment of fees

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