TWI460171B - Diene compounds, epoxy resins and the compositions - Google Patents

Diene compounds, epoxy resins and the compositions Download PDF

Info

Publication number: TWI460171B
Authority: TW; Taiwan
Prior art keywords: acid; compound; epoxy resin; resin composition; reaction
Prior art date: 2009-03-19

Application number

TW099108128A

Other languages

English (en)

Chinese (zh)

Other versions

TW201038549A (en

Inventor

Masataka Nakanishi

Kenichi Kuboki

Naofusa Miyagawa

Yoshihiro Kawada

Chie Sasaki

Shizuka Aoki

Zuikan Suzuki

Masato Yarita

Hiroo Koyanagi

Original Assignee

Nippon Kayaku 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.)

2009-03-19

Filing date

2010-03-19

Publication date

2014-11-11

2010-03-19 Application filed by Nippon Kayaku Kk filed Critical Nippon Kayaku Kk

2010-11-01 Publication of TW201038549A publication Critical patent/TW201038549A/zh

2014-11-11 Application granted granted Critical

2014-11-11 Publication of TWI460171B publication Critical patent/TWI460171B/zh

Links

-1 Diene compounds Chemical class 0.000 title claims description 103
239000003822 epoxy resin Substances 0.000 title claims description 88
229920000647 polyepoxide Polymers 0.000 title claims description 88
239000000203 mixture Substances 0.000 title claims description 29
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 40
239000003054 catalyst Substances 0.000 claims description 14
239000004848 polyfunctional curative Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 8
230000001590 oxidative effect Effects 0.000 claims description 8
150000004965 peroxy acids Chemical class 0.000 claims description 5
239000000463 material Substances 0.000 description 76
239000011342 resin composition Substances 0.000 description 73
239000010408 film Substances 0.000 description 55
238000000034 method Methods 0.000 description 54
230000001070 adhesive effect Effects 0.000 description 49
239000000853 adhesive Substances 0.000 description 48
150000001875 compounds Chemical class 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 44
230000003287 optical effect Effects 0.000 description 41
239000003566 sealing material Substances 0.000 description 39
238000012360 testing method Methods 0.000 description 35
239000000758 substrate Substances 0.000 description 33
238000001723 curing Methods 0.000 description 29
239000011521 glass Substances 0.000 description 29
229920005989 resin Polymers 0.000 description 28
239000011347 resin Substances 0.000 description 28
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
238000010438 heat treatment Methods 0.000 description 25
239000002253 acid Substances 0.000 description 23
239000000047 product Substances 0.000 description 23
239000004065 semiconductor Substances 0.000 description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
239000003960 organic solvent Substances 0.000 description 18
229910052698 phosphorus Inorganic materials 0.000 description 18
239000011574 phosphorus Substances 0.000 description 18
239000000126 substance Substances 0.000 description 17
239000004593 Epoxy Substances 0.000 description 16
229910019142 PO4 Inorganic materials 0.000 description 16
150000008065 acid anhydrides Chemical class 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 16
230000001681 protective effect Effects 0.000 description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000010452 phosphate Substances 0.000 description 15
235000021317 phosphate Nutrition 0.000 description 15
150000003839 salts Chemical class 0.000 description 15
239000002904 solvent Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
239000011248 coating agent Substances 0.000 description 11
238000000576 coating method Methods 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 11
239000002184 metal Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
238000005259 measurement Methods 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 10
239000003505 polymerization initiator Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000654 additive Substances 0.000 description 9
238000005227 gel permeation chromatography Methods 0.000 description 9
239000010410 layer Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
229910002012 Aerosil® Inorganic materials 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
150000003242 quaternary ammonium salts Chemical class 0.000 description 8
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 8
125000002723 alicyclic group Chemical group 0.000 description 7
150000001335 aliphatic alkanes Chemical class 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
239000011256 inorganic filler Substances 0.000 description 7
229910003475 inorganic filler Inorganic materials 0.000 description 7
239000004973 liquid crystal related substance Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
150000002989 phenols Chemical class 0.000 description 7
238000002834 transmittance Methods 0.000 description 7
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 6
NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical class OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
HLVVQXLZWHQZFB-UHFFFAOYSA-N [PH2](O)=O.[PH2](O)=O.C1=CC=C(C=C1)C1=CC=CC=C1 Chemical compound [PH2](O)=O.[PH2](O)=O.C1=CC=C(C=C1)C1=CC=CC=C1 HLVVQXLZWHQZFB-UHFFFAOYSA-N 0.000 description 6
230000000996 additive effect Effects 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
150000007514 bases Chemical class 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
238000012937 correction Methods 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
238000005034 decoration Methods 0.000 description 6
239000012776 electronic material Substances 0.000 description 6
239000002657 fibrous material Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 6
238000002156 mixing Methods 0.000 description 6
239000013307 optical fiber Substances 0.000 description 6
230000002093 peripheral effect Effects 0.000 description 6
229910000073 phosphorus hydride Inorganic materials 0.000 description 6
229920002120 photoresistant polymer Polymers 0.000 description 6
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000001721 transfer moulding Methods 0.000 description 6
239000008096 xylene Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
238000005266 casting Methods 0.000 description 5
238000004891 communication Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
WTNDADANUZETTI-UHFFFAOYSA-N cyclohexane-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1 WTNDADANUZETTI-UHFFFAOYSA-N 0.000 description 5
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
125000003700 epoxy group Chemical group 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000011229 interlayer Substances 0.000 description 5
239000012778 molding material Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 4
JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 4
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
LQOPXMZSGSTGMF-UHFFFAOYSA-N 6004-79-1 Chemical compound C1CC2C3C(=O)OC(=O)C3C1C2 LQOPXMZSGSTGMF-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 4
238000010538 cationic polymerization reaction Methods 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
229910000420 cerium oxide Inorganic materials 0.000 description 4
230000008859 change Effects 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
238000010276 construction Methods 0.000 description 4
230000007797 corrosion Effects 0.000 description 4
238000005260 corrosion Methods 0.000 description 4
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
239000008393 encapsulating agent Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 4
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
229910052750 molybdenum Inorganic materials 0.000 description 4
238000000465 moulding Methods 0.000 description 4
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 4
230000005693 optoelectronics Effects 0.000 description 4
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 4
239000003504 photosensitizing agent Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010926 purge Methods 0.000 description 4
238000010791 quenching Methods 0.000 description 4
230000000171 quenching effect Effects 0.000 description 4
239000002994 raw material Substances 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
238000007789 sealing Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 3
BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 3
SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 3
RGAHHPQKNPTZEY-UHFFFAOYSA-N 2-ethyl-4-methylhexane-1,1-diol Chemical compound CCC(C)CC(CC)C(O)O RGAHHPQKNPTZEY-UHFFFAOYSA-N 0.000 description 3
DGQFNPWGWSSTMN-UHFFFAOYSA-N 2-tert-butyl-4-[4-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1CCCCC1=CC(C(C)(C)C)=C(O)C=C1C DGQFNPWGWSSTMN-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920000049 Carbon (fiber) Polymers 0.000 description 3
229910052684 Cerium Inorganic materials 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229920000459 Nitrile rubber Polymers 0.000 description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
235000006708 antioxidants Nutrition 0.000 description 3
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238000012546 transfer Methods 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
ZBZIRIODYXOQSJ-UHFFFAOYSA-N trihexadecyl(methyl)azanium Chemical class CCCCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC ZBZIRIODYXOQSJ-UHFFFAOYSA-N 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
DCAFJGSRSBLEPX-UHFFFAOYSA-N tris(2,3-dibutylphenyl) phosphite Chemical compound CCCCC1=CC=CC(OP(OC=2C(=C(CCCC)C=CC=2)CCCC)OC=2C(=C(CCCC)C=CC=2)CCCC)=C1CCCC DCAFJGSRSBLEPX-UHFFFAOYSA-N 0.000 description 1
OOZKMYBQDPXENQ-UHFFFAOYSA-N tris(2,3-diethylphenyl) phosphite Chemical compound CCC1=CC=CC(OP(OC=2C(=C(CC)C=CC=2)CC)OC=2C(=C(CC)C=CC=2)CC)=C1CC OOZKMYBQDPXENQ-UHFFFAOYSA-N 0.000 description 1
AJHKJOCIGPIJFZ-UHFFFAOYSA-N tris(2,6-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1OP(OC=1C(=CC=CC=1C(C)(C)C)C(C)(C)C)OC1=C(C(C)(C)C)C=CC=C1C(C)(C)C AJHKJOCIGPIJFZ-UHFFFAOYSA-N 0.000 description 1
WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1
RSJKGSCJYJTIGS-BJUDXGSMSA-N undecane Chemical compound CCCCCCCCCC[11CH3] RSJKGSCJYJTIGS-BJUDXGSMSA-N 0.000 description 1
229940096998 ursolic acid Drugs 0.000 description 1
PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
238000005406 washing Methods 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
229910052727 yttrium Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1
229940105125 zinc myristate Drugs 0.000 description 1
JRHDFVNUWLMGBU-UHFFFAOYSA-L zinc octyl phosphate Chemical compound C(CCCCCCC)OP(=O)([O-])[O-].[Zn+2] JRHDFVNUWLMGBU-UHFFFAOYSA-L 0.000 description 1
IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
IJQXGKBNDNQWAT-UHFFFAOYSA-L zinc;docosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O IJQXGKBNDNQWAT-UHFFFAOYSA-L 0.000 description 1
PORPEXMDRRVVNF-UHFFFAOYSA-L zinc;octadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCOP([O-])([O-])=O PORPEXMDRRVVNF-UHFFFAOYSA-L 0.000 description 1
GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
229910052845 zircon Inorganic materials 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Epoxy Resins (AREA)
Plural Heterocyclic Compounds (AREA)

TW099108128A 2009-03-19 2010-03-19 Diene compounds, epoxy resins and the compositions TWI460171B (zh)

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JP2009067197		2009-03-19

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JP (1)	JP5492081B2 (ja)
KR (1)	KR20110135917A (ja)
CN (1)	CN102333768B (ja)
TW (1)	TWI460171B (ja)
WO (1)	WO2010107085A1 (ja)

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JP5519685B2 (ja) *	2009-10-09	2014-06-11	日本化薬株式会社	硬化性樹脂組成物、及びその硬化物
CN103554440B (zh) *	2013-10-12	2017-01-25	瑞奇化工（松滋）有限公司	一种改性芳香胺固化剂及其制备方法
KR102332174B1 (ko) *	2014-04-15	2021-12-01	미쯔비시 가스 케미칼 컴파니, 인코포레이티드	섬유강화 복합재료
WO2016119848A1 (en) *	2015-01-29	2016-08-04	Henkel Ag & Co. Kgaa	Method for the preparation of cycloaliphatic epoxy resins

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JPS62241979A (ja) *	1986-04-15	1987-10-22	Nippon Kayaku Co Ltd	樹脂組成物及びソルダ−レジストインキ組成物
JP2006052187A (ja) *	2004-08-16	2006-02-23	Daicel Chem Ind Ltd	脂環式オレフィン化合物および脂環式エポキシ化合物の製造方法
JP2007126447A (ja) *	2005-10-04	2007-05-24	Mitsubishi Gas Chem Co Inc	ジオキサングリコールの製造方法

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Publication number	Priority date	Publication date	Assignee	Title
WO2010041670A1 (ja) *	2008-10-06	2010-04-15	日本化薬株式会社	ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物、および硬化物

2010
- 2010-03-18 KR KR1020117016000A patent/KR20110135917A/ko not_active Abandoned
- 2010-03-18 JP JP2010520367A patent/JP5492081B2/ja not_active Expired - Fee Related
- 2010-03-18 WO PCT/JP2010/054669 patent/WO2010107085A1/ja not_active Ceased
- 2010-03-18 CN CN201080009581.5A patent/CN102333768B/zh not_active Expired - Fee Related
- 2010-03-19 TW TW099108128A patent/TWI460171B/zh active

Patent Citations (3)

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Publication number	Priority date	Publication date	Assignee	Title
JPS62241979A (ja) *	1986-04-15	1987-10-22	Nippon Kayaku Co Ltd	樹脂組成物及びソルダ−レジストインキ組成物
JP2006052187A (ja) *	2004-08-16	2006-02-23	Daicel Chem Ind Ltd	脂環式オレフィン化合物および脂環式エポキシ化合物の製造方法
JP2007126447A (ja) *	2005-10-04	2007-05-24	Mitsubishi Gas Chem Co Inc	ジオキサングリコールの製造方法

Also Published As

Publication number	Publication date
CN102333768B (zh)	2014-11-12
TW201038549A (en)	2010-11-01
CN102333768A (zh)	2012-01-25
WO2010107085A1 (ja)	2010-09-23
KR20110135917A (ko)	2011-12-20
JP5492081B2 (ja)	2014-05-14
JPWO2010107085A1 (ja)	2012-09-20

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