JPS6331493B2 - - Google Patents
Info
- Publication number
- JPS6331493B2 JPS6331493B2 JP2769384A JP2769384A JPS6331493B2 JP S6331493 B2 JPS6331493 B2 JP S6331493B2 JP 2769384 A JP2769384 A JP 2769384A JP 2769384 A JP2769384 A JP 2769384A JP S6331493 B2 JPS6331493 B2 JP S6331493B2
- Authority
- JP
- Japan
- Prior art keywords
- curing
- formula
- epoxy
- group
- epoxy resin
- 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.)
- Expired
Links
- 239000003822 epoxy resin Substances 0.000 claims description 41
- 229920000647 polyepoxide Polymers 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 31
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 239000003063 flame retardant Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 32
- 230000009102 absorption Effects 0.000 description 28
- 238000010521 absorption reaction Methods 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 20
- 125000003700 epoxy group Chemical group 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 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 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 12
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000002723 alicyclic group Chemical group 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- -1 Aliphatic alcohols Chemical class 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000011417 postcuring Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- FKBMTBAXDISZGN-UHFFFAOYSA-N 5-methyl-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1C(C)CCC2C(=O)OC(=O)C12 FKBMTBAXDISZGN-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 4
- 150000004965 peroxy acids Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012045 crude solution Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tertâbutyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- 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 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- 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 1
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- NIYNIOYNNFXGFN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound OCC1CCC(CO)CC1.C1C(C(=O)O)CCC2OC21.C1C(C(=O)O)CCC2OC21 NIYNIOYNNFXGFN-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 231100001068 severe skin irritation Toxicity 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 239000013638 trimer Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
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The present invention relates to a novel epoxy resin composition with excellent heat resistance, water resistance, and weather resistance. The epoxy resin currently most widely used in industry is the epi-bis type epoxy resin, which is produced by the reaction of bisphenol A and epichlorohydrin. This resin can be used in a wide variety of products ranging from liquids to solids, and has the advantage that the epoxy group has high reactivity and can be cured with polyamines at room temperature. However, although the cured product has excellent water resistance and is strong, it has drawbacks such as poor weather resistance, poor electrical properties such as tracking resistance, and low heat distortion temperature. Especially recently, super LSI
Epoxy resin made by reacting phenol or novolac resin with epichlorohydrin is used as sealing resin, but the resin contains several hundred ppm of chlorine.
This has caused problems such as deterioration of the electrical characteristics of electronic components. Alicyclic epoxy resins are examples of epoxy resins that do not contain chlorine and have excellent electrical properties and heat resistance. These are produced by epoxidation reaction of compounds having a 5-membered or 6-membered cycloalkenyl skeleton. The epoxy groups of these resins are so-called internal epoxy groups, and are usually cured by heating with acid anhydrides, but cannot be cured at room temperature with polyamines because of their low reactivity. Therefore, the range of use of alicyclic epoxy resins is extremely narrow. As alicyclic epoxy resins, those having the structures () and () are industrially produced and used. () is used as a heat-resistant epoxy diluent because of its extremely low viscosity, but it is highly toxic.
There are problems such as severe skin irritation of workers. () contains few impurities and has a low hue, and its cured product has a high heat deformation temperature and has a problem of poor water resistance due to the ester bond. Furthermore, since both () and () are low-viscosity liquid epoxy resins, solid epoxy resin molding systems such as transfer molding cannot be applied. In view of these problems, the present inventors conducted intensive research to develop a new epoxy resin, and as a result, they found that it is an alicyclic type, can be in any state from liquid to solid, and has excellent water resistance and heat resistance. and found an epoxy resin composition having excellent reactivity,
The present invention has now been accomplished. That is, the present invention comprises an epoxy resin represented by the following general formula, a curing agent, and optionally a filler.
This invention relates to a novel epoxy resin composition characterized by containing a flame retardant and various other additives. However, R 1 is a monovalent or higher alcohol having 1 active hydrogens or an unsaturated compound residue having a hydroxyl group. n 1 , n 2 . . . n l is 0 or an integer of 1 to 100, and the sum thereof is 1 to 100. l represents an integer from 1 to 100. A is an oxycyclohexane skeleton having a substituent X, and is represented by the following formula. The substituent X is
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åŒïŒïŒã«ãããã®çœ®æåºïŒžã®ãã¡ãThe resin represented by () contains one or more of the following formulas: Next, the present invention will be explained in detail. In the novel epoxy resin represented by the formula () of the present invention, R 1 is a monohydric or more alcohol having l active hydrogens or an unsaturated compound residue having a hydroxyl group, but the precursor active hydrogen is Examples of the organic substances include alcohols, phenols, carboxylic acids, amines, and thiols. The alcohol may be a monohydric alcohol or a polyhydric alcohol. For example, methanol, ethanol, propanol, butanol, pentanol, hexanol,
Aliphatic alcohols such as octanol, aromatic alcohols such as benzyl alcohol, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, 1,3
Butanediol, 1,4 butanediol, pentanediol, 1,6 hexanediol, neopentyl glycol, oxypivalic acid neopentyl glycol ester, cyclohexanedimethanol, glycerin, diglycerin, polyglycerin, trimethylolpropane, trimethylolethane, Examples include polyhydric alcohols such as pentaerythritol and dipentaerythritol. Further, the compound having active hydrogen may have an unsaturated double bond in its skeleton, and specific examples include allyl alcohol, acrylic acid, and methacrylic acid. The unsaturated double bonds of these compounds may also have an epoxidized structure. n 1 , n 2 ... n l in general formula () is 0 or 1
~100, and the sum thereof is 1 to 100, but if it exceeds 100, it becomes a resin with a high melting point and is difficult to handle, making it practically unusable. l is an integer from 1 to 100. Among the substituents X of A in formula (),
ãåŒããå°ãªããšãïŒå以äžå«ãããšãå¿ é ã§ãããMust include at least one [formula] Although it is
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åã®ãšããã·åãšåæã«åæäžã®çœ®æåº[Formula] is the main one. Specifically, the novel epoxy resin represented by the formula () of the present invention is a polyether resin obtained by ring-opening polymerization of 4-vinylcyclohexene-1-oxide using an organic compound having active hydrogen as an initiator. That is, it can be produced by epoxidizing a polycyclohexene oxide polymer having a vinyl group side chain with an oxidizing agent such as a peracid. 4-Vinylcyclohexene-1-oxide can be obtained by partially epoxidizing vinylcyclohexene obtained by dimerization of butadiene with peracetic acid. It is preferable to use a catalyst when 4-vinylcyclohexene-1-oxide is polymerized in the presence of active hydrogen. Examples of catalysts include amines such as methylamine, ethylamine, propylamine, and piperazine; organic bases such as pyridines and imidazoles; organic acids such as formic acid, acetic acid, and propionic acid; inorganic acids such as sulfuric acid and hydrochloric acid; and sodium methylate. alcoholates of alkali metals, alkalis such as KOH and NaOH, Lewis acids such as BF 3 , ZnCl 2 , AlCl 3 and SnCl 4 or their complexes, and organometallic compounds such as triethylaluminum and diethylzinc. Can be done. These catalysts can be used in an amount of 0.01 to 10%, preferably 0.1 to 5%, based on the reactants. Reaction temperature is -70~200â, preferably -30â
~100â. The reaction can also be carried out using a solvent. A solvent containing active hydrogen cannot be used. That is, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, aromatic solvents such as benzene, toluene, and xylene, as well as ethers, aliphatic hydrocarbons, esters, and the like can be used. Now, in order to epoxidize the polycyclohexene oxide polymer having vinyl group side chains synthesized in this way and to produce the new epoxy resin of the formula () of the present invention, either peracids or hydroperoxides are used. Can be used. As peracids, performic acid, peracetic acid, perbenzoic acid, trifluoroperacetic acid, etc. can be used. Among these, peracetic acid is a particularly preferred epoxidizing agent because it is industrially available at low cost and has high stability. Hydroperoxides include hydrogen peroxide, tertiary butyl hydroperoxide,
Cumene peroxide etc. can be used. A catalyst can be used during epoxidation if necessary. For example, in the case of a peracid, an alkali such as soda carbonate or an acid such as sulfuric acid may be used as a catalyst. In the case of hydroperoxides, the catalytic effect can also be obtained by using a mixture of tungstic acid and caustic soda with hydrogen peroxide, an organic acid with hydrogen peroxide, or molybdenum hexacarbonyl with tertiary butyl hydroperoxide. . The epoxidation reaction is carried out by adjusting the presence or absence of a solvent and the reaction temperature depending on the equipment and physical properties of the raw materials. Depending on the conditions of the epoxidation reaction, olefin bonds can be epoxidized and substituents in the raw materials can be
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ã«OHåºã1730cm-1ã«ã[Formula] and the ratio of the three modified substituents are determined by the type of epoxidizing agent, the molar ratio of the epoxidizing agent to the olefin bond, and the reaction conditions. For example, when the epoxidizing agent is peracetic acid, the modified substituent mainly has the structure shown below, and is generated from the generated epoxy group and by-produced acetic acid. The target compound can be taken out from the reaction crude solution by ordinary chemical industrial means such as concentration.
Furthermore, the epoxy resin used in the present invention can be mixed with other epoxy resins as long as the properties of the composition are not impaired. Here, other epoxy resins may be any commonly used epoxy resins, such as epibis epoxy, bisphenol F epoxy, novolac epoxy, alicyclic epoxy, and epoxy resins such as styrene oxide and butyl glycidyl ether. Contains diluent. As the curing agent used in the present invention, curing agents used in known epoxy resins can be used, including amines, polyamide resins, acid anhydrides, polymercaptan resins, novolac resins, dicyandiamide,
This includes amine complexes of boron trifluoride. Here, the amines include the following. Aliphatic polyamines such as diethylenetriamine, triethylenetetramine, menzendiamine, metaxylylenediamine, bis(4-amino-3-methylcyclohexyl)methane, adducts of the aliphatic polyamines with known epoxy compounds, and reactions with acrylonitrile. substances, reactants with ketones. Aromatic polyamines such as metaphenylene diamine, diaminodiphenylmethane, diaminodiphenyl sulfone, diaminodiphenyl sulfide, and adducts of the aromatic polyamines and known epoxy compounds. tris(dimethylaminomethyl)phenol,
Secondary and tertiary amines and salts thereof such as piperidine, imidazole and derivatives thereof. and mixtures of the aforementioned amines. Polyamide resins include reactants of fatty acids, such as fatty acids, dimer acids, trimer acids, and aliphatic polyamines. Acid anhydrides include the following: Phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic dianhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, Acid anhydrides such as succinic anhydride, dodecenylsuccinic anhydride, succinic anhydride, and mixtures of the above acid anhydrides. Novolac resins include low molecular weight resinous products made by the condensation of phenols or mixtures of phenols and cresols, dihydroxybenzenes, and formaldehyde. Amine complexes of boron trifluoride include complexes of boron trifluoride and low molecular weight amine compounds such as monoethylamine, piperidine, aniline, butylamine, dibutylamine, cyclohexylamine, dicyclohexylamine, tributylamine, and triethanolamine. It will be done. In addition, other hardening agents include boron tetrafluoride,
There are salts such as diazonium salts, iodonium salts, bromonium salts, and sulfinium salts of super strong acids such as phosphorus hexafluoride and arsenic hexafluoride. Also, among these curing agents, aliphatic polyamines, aromatic polyamines,
Polyamide resins and polymercaptan resins can be used as a mixture in any proportion, and can be used alone or in combination with a curing accelerator for the purpose of adjusting the curing rate. Here, the aforementioned secondary and tertiary amines can be used as the curing accelerator. The acid anhydride can be used as it is, but a curing catalyst and a curing accelerator can also be used together for the purpose of adjusting the curing rate and improving the physical properties of the cured product.
Here, the curing catalysts are the aforementioned secondary and tertiary amines and tin octylate. Curing accelerators include water, alcohols such as ethanol, propanol, isopropanol, cyclohexanol, and ethylene glycol, carboxylic acids such as acetic acid, propionic acid, succinic acid, and hexahydrophthalic acid, and active hydrogen such as ethylenediamine and diethylenetriamine. They are amines. The novolak resin can be used alone or in combination with a curing catalyst for the purpose of adjusting the curing rate. Here, the curing catalysts are the aforementioned secondary and tertiary amines. Dicyandiamide can be used alone or in combination with a curing catalyst for the purpose of adjusting the curing rate. Here, the curing catalysts are the aforementioned secondary and tertiary amines. The amine complex of boron trifluoride can be used alone or in combination with a curing rate regulator for the purpose of adjusting the curing rate. Here, any curing rate regulator may be used as long as it can be used in conventional epoxy resins, but specific examples include carboxylic acids, amines, acetylacetone complexes of metals, metals such as titanium, tin, etc. These include organometallic compounds, glycols, organoboron compounds, etc. The filler used in the present invention may be anything as long as it can be used as a filler for resin, but specific examples include silica sand, silica, alumina,
These include diatomaceous earth, calcium carbonate, asbestos, glass, magnesium carbonate, kaolin, metal powder, etc. Various shapes can be used, such as fibrous, flake, etc. Any flame retardant may be used as long as it can be used as a flame retardant for resins, but specific examples include halides such as tetrabromobisphenol A, hexabromobenzene, tris(dibromopropyl) phosphate, and trischloro. Examples include phosphorus compounds such as ethyl phosphate, antimony trioxide, etc. Various other additives can be used in combination depending on the purpose, such as thixotropy imparting agents such as Aerosil and Olben, conductivity imparting agents such as carbon black, etc.
There are mold release agents, lubricants, dyes, pigments, coupling agents, flexibility agents, plasticizers, etc., and they can also be used after being diluted with a solvent. By molding and curing the resin composition obtained in this way, a cured product with excellent mechanical properties such as tensile strength and hardness, electrical properties such as tracking resistance and arc resistance, and heat distortion temperature and low corrosivity can be obtained. Encapsulants for electronic parts, encapsulants for light emitting diodes, insulating varnishes for motors, transformers, etc., fiber-reinforced plastics, adhesives, powder coatings, electrodeposition coatings, printed circuit boards, cast materials, moldings. It can be used for things etc. The present invention will be further explained in detail by giving examples below. Synthesis example 1 Allyl alcohol 116g (2 mol), 4-vinylcyclohexene-1-oxide 496g (4 mol)
and 3.1 g of BF 3 etherate were mixed at 60° C. and reacted until the conversion of 4-vinylcyclohexene-1-oxide reached 98% or more as determined by gas chromatography analysis. Ethyl acetate was added to the resulting reaction crude liquid, washed with water, and then the ethyl acetate layer was concentrated to obtain a viscous liquid. In the infrared absorption spectrum of the product, the absorption due to epoxy groups at 810 and 850 cm -1 observed in the raw material has disappeared, and absorption due to ether bonds exists at 1080 and 1150 cm -1 , and gas chromatography analysis shows that Allyl alcohol in the product is a trace amount, but in the infrared absorption spectrum it is 3450cm
It was confirmed that this compound has the structure shown by the following formula from the absorption of OH group at -1 . 434 g of this compound was dissolved in ethyl acetate and charged into a reactor, to which 388 g of peracetic acid was added dropwise as an ethyl acetate solution over 2 hours. During this time, the reaction temperature was maintained at 40°C. After the completion of peracetic acid preparation, 40
It was further aged for 6 hours at °C. Add ethyl acetate to the reaction crude solution and add sodium carbonate.
It was washed with alkaline water containing 416 g, followed by thorough washing with distilled water. The ethyl acetate layer was concentrated to obtain a viscous clear liquid. This compound has an oxirane oxygen content of 9.97%
In the infrared absorption spectrum, characteristic absorption due to epoxy groups was observed at 1260 cm -1 . Furthermore, absorption due to residual vinyl groups is observed at 1640 cm -1 and 3450 cm -1
OH group, 1730 cm -1 ,
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(1 mol), 868 g (7 mol) of 4-vinylcyclohexene-1-oxide, and 4.7 g of BF 3 etherate were reacted to obtain a viscous liquid product. In the infrared absorption spectrum of the product, the absorption by epoxy groups at 810 and 850 cm -1 observed in the raw material disappeared, and the presence of absorption due to ether bonds at 1080 and 1150 cm -1 , gas chromatography analysis showed that Allyl alcohol in the product is a trace amount, but in the infrared absorption spectrum it is 3450cm
It was confirmed that this compound had the structure shown by the following formula from the presence of absorption of OH group at -1 . Further, 49.2 g of this compound was reacted with 395 g of peracetic acid in the same manner as in Example 1 to obtain a viscous transparent liquid. This compound has an oxirane oxygen content of 9.27%
In the infrared absorption spectrum, characteristic absorption due to epoxy groups was observed at 1260 cm -1 . Furthermore, 1640cm -1
Absorption due to residual vinyl groups is observed in 3450
OH group at cm -1 , 1730 cm -1
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-Vinylcyclohexene-1-oxide 744g
4.1 g of BF 3 etherate was reacted to obtain a viscous liquid product. In the infrared absorption spectrum of the product, the absorption due to epoxy groups at 810 and 850 cm -1 observed in the raw material has disappeared, and absorption due to ether bonds exists at 1080 and 1150 cm -1 , and gas chromatography analysis shows that , the methanol in the product is a trace amount, but the infrared absorption spectrum shows it to be 3450 cm -1
The absorption of OH groups confirmed that this compound had the structure shown by the following formula. Further, 573 g of this compound and 387 g of peracetic acid were reacted in the same manner as in Synthesis Example 1 to obtain a viscous transparent liquid. This compound has an oxirane oxygen content of 9.03%
In the infrared absorption spectrum, characteristic absorption due to epoxy groups was observed at 1260 cm -1 . Furthermore, 1640cm -1
Absorption due to residual vinyl groups is observed in 3450
OH group in cm, 1730 cm -1
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cm-1ã«OHåºã1730cm-1ã«[Table] Synthesis Example 4 32 g (1 mol) of methanol, 868 g (7 mol) of 4-vinylcyclohexene-1-oxide, and 9.2 g of BF 3 etherate were mixed at 60°C, and 4-vinylcyclohexene-1 was determined by gas chromatography analysis. -The reaction was allowed to occur until the oxide conversion rate reached 98% or higher. Ethyl acetate was added to the obtained reaction crude liquid and washed with water, and then the ethyl acetate layer was concentrated to obtain a viscous liquid. In the infrared absorption spectrum of the product, the absorption by epoxy groups at 810 and 850 cm -1 observed in the raw material disappeared, and the presence of absorption due to ether bonds at 1080 and 1150 cm -1 , and gas chromatography analysis revealed that , the amount of allyl alcohol in the product is only trace, but it is 3450 in the infrared absorption spectrum.
It was confirmed that this compound has the structure shown by the following formula from the absorption of OH group at cm -1 . 434 g of this compound was dissolved in ethyl acetate and charged into a reactor, to which 388 g of peracetic acid was added dropwise as an ethyl acetate solution over 2 hours. During this time, the reaction temperature was maintained at 40°C. After the completion of peracetic acid preparation, 40
It was aged for an additional 6 hours at °C. Add ethyl acetate to the reaction crude solution and add sodium carbonate.
It was washed with alkaline water containing 416 g, followed by thorough washing with distilled water. The ethyl acetate layer was concentrated to obtain a solid resin at room temperature. This compound has an oxirane oxygen content of 9.97%
In the infrared absorption spectrum, characteristic absorption due to epoxy groups was observed at 1260 cm -1 . Furthermore, 1640cm -1
Absorption due to residual vinyl groups is observed in 3450
OH group at cm -1 , 1730 cm -1
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Since absorption by the [Formula] group is observed, this compound has the structure of the general formula () (R: glycidyl group or allyl group, n = average 2, contains a small amount of acetic acid added to an epoxy group). confirmed. Example 1 A curing agent was added to the products of Synthesis Examples 1, 2, and 3, and the gel time was measured to examine the curability of the epoxy resin. A novolak type phenol resin (PSF-4300 Gunei Chemical Industry Co., Ltd.) was used as a curing agent, and 2-undecylimidazole (Kyuazol C 11 Z, Shikoku Kasei Kogyo Co., Ltd.) was used as a curing catalyst. or,
3,4-epoxycyclohexylmethyl, a typical alicyclic epoxy resin, was used as a comparison resin.
Using 3',4'-epoxycyclohexanecarboxylate (Celoxide 2021, Daicel Chemical Industries, Ltd.), blend it according to the following formulation, melt and mix at 120°C for about 1 minute, then cool and mix. Obtained.
The gel time of the obtained formulation at 120°C was measured according to JIS-C2104-7 (hot plate method), and the results shown in Table 2 were obtained. It can be seen that the resin of the present invention has higher curability than conventional alicyclic epoxy resins. Compounding formula Epoxy resin 1.0 equivalent PSF-4300 1.1 equivalent Kyuazol C 11 Z (based on the compound) 0.7% by weight
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[Table] Example 2 Using the compounds of Synthesis Examples 1, 2, and 3, physical properties of cured products were measured. Using the same curing agent and curing catalyst as in Example 1, the following formulation was mixed in the same manner as in Example 1 to obtain a mixture. The resulting mixture was pulverized and press-molded to obtain a test piece. Molding is 90
~30â from 60â to 170â under pressure of ~100Kgf/ cm2
After heating at 170â for 10 minutes under pressure,
Post-curing was carried out for 2 hours in an oven set at .degree. The obtained cured product was cut into test pieces, and the physical properties were measured according to JIS-K-6911.
The results shown in Table 3 were obtained. Compounding formula Epoxy resin 1.0 equivalent PSF-4300 0.9 equivalent Kyuazol C 11 Z (based on the compound) 0.7% by weight
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MHâ700 0.8åœé[Table] Example 3 4-Methylhexahydrophthalic anhydride (Rikacid MH-700,
Curing was performed using Shin Nippon Rika Co., Ltd.). In addition, 3,4-epoxycyclohexylmethyl-3', which is a typical alicyclic epoxy resin, was used as a comparison resin.
Using 4'-epoxycyclohexanecarboxylate (Celoxide 2021, Daicel Chemical Industries, Ltd.), mix the following formulation, melt and mix at 80â for about 5 minutes, degas under reduced pressure, and harden by casting. A cured product was obtained. Curing in oven at 160â
Pre-curing was carried out at 180° C. for 1 hour, and post-curing was further carried out for 2 hours at 180°C. The obtained cured product was cut into test pieces, and the heat distortion temperature was measured according to JIS-K-6911, and the results shown in Table 4 were obtained. Compounding formula Epoxy resin 1.0 equivalent MH-700 0.8 equivalent
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[Table] Example 4 4-Methylhexahydrophthalic anhydride (Rikacid MH) was added to the products of Synthesis Examples 1 and 2 as a curing agent.
-700, Shin Nippon Chemical Co., Ltd.) and benzyldimethylamine as a curing catalyst. or,
3,4-epoxycyclohexylmethyl, a typical alicyclic epoxy resin, was used as a comparison resin.
Using 3,4-epoxycyclohexanecarboxylate (Celoxide 2021, Daicel Chemical Industries, Ltd.), the following formulation was used to compound
After melting and mixing for a minute, the mixture was defoamed under reduced pressure and cured by casting to obtain a cured product. Curing in the oven
Pre-curing was carried out at 100°C for 1 hour, and post-curing was further carried out at 160°C for 2 hours. The obtained cured product was cut into test pieces, and the heat distortion temperature was measured according to JIS-K-6911, and the results shown in Table 5 were obtained. Mixing recipe Epoxy resin 1.0 equivalent MH-700 0.9 equivalent Benzyldimethylamine (based on the mixture) 0.5% by weight
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[Table] Example 5 4-Methylhexahydrophthalic anhydride (Rikacid MH-700,
Curing was carried out using Shin Nippon Chemical Co., Ltd.) and benzyldimethylamine as a curing catalyst. In addition, as a comparative resin, 3,4-epoxycyclohexylmethyl-3', which is a typical alicyclic epoxy resin,
Using 4'-epoxycyclohexane carboxylate (Celoxide 2021, Daicel Chemical Industries, Ltd.) and bisphenol A diglycidyl ether (Epicote 828, Yuka Ciel Epoxy Co., Ltd.), a general epoxy resin, the following formulation was prepared. After mixing at 80° C. for about 5 minutes, the mixture was degassed under reduced pressure and cured by casting to obtain a cured product. For curing, pre-cure in an oven at 100â for 1 hour, then further cure at 160â.
Post-curing was carried out for 2 hours at °C. The obtained cured product was cut into test pieces, and the physical properties were measured according to JIS-K-6911.
The results shown in Table 6 were obtained. As is clear from the table, the resin of the present invention has good heat resistance and excellent electrical properties. Compounding recipe Epoxy resin 1 equivalent MH-700 1 equivalent Benzyldimethylamine (based on the compound) 0.5%
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MHâ700[Table] Example 6 The product of Synthesis Example 4 was added with 4-methylhexahydrophthalic anhydride (Rikacid MH-700,
Curing was performed using Shin Nippon Rika Co., Ltd.). In addition, as in Example 5, Celoxide 2021 was used as a comparative resin.
and Epicote 828 were mixed according to the following formulation, mixed at 80°C for about 5 minutes, defoamed under reduced pressure, and cured by casting to obtain a cured product. Precuring was performed in an oven at 130°C for 1 hour.
Celloxide 2021 and Epicote 828 were still in liquid form at this stage, so they were heated at 130°C for an additional 2 hours (3 hours in total), but no gelation was observed, so they were heated at 140°C for an additional hour. Where I went,
Gelation was observed in Celloxide 2021. After pre-curing under the above conditions, post-curing was carried out at 180° C. for 2 hours, but no cured product could be obtained with Epikote 828. The obtained cured product was cut into a test piece, and its physical properties were measured according to JIS-K-6911.
The obtained cured product was cut into test pieces,
Physical properties were measured according to JIS-K-6911, and Table 7
I got the result. As is clear from the table, the resin of the present invention has good heat resistance and excellent electrical properties. Mixing prescription Epoxy resin 1 equivalent MH-700
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[Table] Synthesis Example 5 134 g (1 mol) of trimethylolpropane and 1863 g (15 mol) of vinylcyclohexene monoepoxide were reacted in the same manner as in Example 1 to obtain a product. When the obtained product was analyzed by elemental analysis, IR, and NMR, it was confirmed that it had the structure shown by the formula (). In the IR analysis, 810, 850 and
The absorption of epoxy group at 1850cm -1 disappears and the absorption becomes 1080cm -1
The absorption of the ether bond was newly generated. Furthermore, absorptions of vinyl groups at 910 cm -1 and 1640 cm -1 remain. In NMR, a peak similar to that in Example 1 was confirmed. The elemental analysis values are shown below. C H Analytical value 76.05 9.65 Theoretical value 75.82 9.73 From the above results, the structure of formula () was confirmed. Example 7 Using the compound of Synthesis Example 5 and cresol novolac epoxy (Toto Kasei, YDCN-702), the physical properties of the cured product were measured. Using the same curing agent and curing catalyst as in Example 1, the following formulation was mixed in the same manner as in Example 1 to obtain a mixture. The resulting mixture was pulverized and press-molded to obtain a test piece. Molding is 90
~30â from 60â to 170â under pressure of ~100Kgf/ cm2
After heating at 170â for 10 minutes under pressure,
Post-curing was carried out for 2 hours in an open set at .degree. The obtained cured product was cut into test pieces, and the physical properties were measured according to JIS-K-6911.
The results shown in Table 8 were obtained. Compounding formula Epoxy resin 1.0 equivalent PSF-4300 1.0 equivalent Kyuazol C 11 Z (based on the compound) 0.7% by weight
Claims (1)
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以äžå«ãïŒã[Claims] 1. A novel epoxy resin represented by the general formula (), a curing agent, and optionally a filler, a flame retardant,
An epoxy resin composition characterized by containing various other additives. However, R 1 is a residue of an organic compound having l active hydrogens, and the organic compound is one or a mixture of two or more selected from monohydric or more alcohols or unsaturated compounds having a hydroxyl group. n1, n2...nl are each 0 or an integer between 1 and 100, and their sum is between 1 and 100. l represents an integer from 1 to 100. A is an oxycyclohexane skeleton having a substituent, and is represented by the following formula. X is [formula]-CH=CH 2 R 2 is H, an alkyl group, an alkylcarbonyl group,
Any one of the arylcarbonyl groups, The resin represented by the formula () contains at least one or more of the following.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2769384A JPS60170620A (en) | 1984-02-16 | 1984-02-16 | Novel epoxy resin composition |
| US06/696,239 US4565859A (en) | 1984-01-30 | 1985-01-29 | Polyether compounds, epoxy resins, epoxy resin compositions, and processes for production thereof |
| DE8585100950T DE3586597T2 (en) | 1984-01-30 | 1985-01-30 | POLYETHER COMPOUNDS AND METHOD FOR THEIR PRODUCTION. |
| EP85100950A EP0150850B1 (en) | 1984-01-30 | 1985-01-30 | Polyether compounds and processes for production thereof |
| JP18970287A JPH01152119A (en) | 1984-02-16 | 1987-07-29 | Epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2769384A JPS60170620A (en) | 1984-02-16 | 1984-02-16 | Novel epoxy resin composition |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18970287A Division JPH01152119A (en) | 1984-02-16 | 1987-07-29 | Epoxy resin composition |
| JP22472187A Division JPS6372721A (en) | 1987-09-08 | 1987-09-08 | Epoxy resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60170620A JPS60170620A (en) | 1985-09-04 |
| JPS6331493B2 true JPS6331493B2 (en) | 1988-06-24 |
Family
ID=12228045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2769384A Granted JPS60170620A (en) | 1984-01-30 | 1984-02-16 | Novel epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60170620A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62207320A (en) * | 1986-03-07 | 1987-09-11 | Hitachi Ltd | Theromosetting resin composition and semiconductor device coated or sealed therewith |
| JPH07119270B2 (en) * | 1986-09-01 | 1995-12-20 | ãã€ã»ã«ååŠå·¥æ¥æ ªåŒäŒç€Ÿ | Epoxy resin |
| JPH0558377U (en) * | 1992-01-10 | 1993-08-03 | æ ªåŒäŒç€ŸåŠç¿ç 究瀟 | Knocking writing instrument |
| CA2107337A1 (en) * | 1992-01-31 | 1993-08-01 | Toshio Fujibayashi | Resin composition for aqueous coating |
| CA2108075A1 (en) * | 1992-10-09 | 1994-04-10 | Toshio Fujibayashi | Resin composition for aqueous paint |
| JP4473755B2 (en) | 2005-03-17 | 2010-06-02 | é¢è¥¿ãã€ã³ãæ ªåŒäŒç€Ÿ | Electrodeposition paint, painting method and article |
-
1984
- 1984-02-16 JP JP2769384A patent/JPS60170620A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60170620A (en) | 1985-09-04 |
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