JPS6244564B2 - - Google Patents
Info
- Publication number
- JPS6244564B2 JPS6244564B2 JP8087779A JP8087779A JPS6244564B2 JP S6244564 B2 JPS6244564 B2 JP S6244564B2 JP 8087779 A JP8087779 A JP 8087779A JP 8087779 A JP8087779 A JP 8087779A JP S6244564 B2 JPS6244564 B2 JP S6244564B2
- Authority
- JP
- Japan
- Prior art keywords
- resin composition
- triazine
- parts
- resins
- 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
- 239000011342 resin composition Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 10
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
- REWLXMVGEZMKSG-UHFFFAOYSA-N 3-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC(O)=C1 REWLXMVGEZMKSG-UHFFFAOYSA-N 0.000 claims description 7
- JAPJPKKYCWSYIR-UHFFFAOYSA-N 2-[(3-prop-1-en-2-ylphenoxy)methyl]oxirane Chemical compound CC(=C)C1=CC=CC(OCC2OC2)=C1 JAPJPKKYCWSYIR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229940126062 Compound A Drugs 0.000 description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 230000000052 comparative effect Effects 0.000 description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000843 powder Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- -1 diethyl Tertiary amines Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 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 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000002648 laminated material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical group N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 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 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
- DQJPVGLHHIGXJL-UHFFFAOYSA-N 2-[(2-prop-1-en-2-ylphenoxy)methyl]oxirane Chemical compound CC(=C)C1=CC=CC=C1OCC1OC1 DQJPVGLHHIGXJL-UHFFFAOYSA-N 0.000 description 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- WHGXZPQWZJUGEP-UHFFFAOYSA-N 2-prop-1-enylphenol Chemical compound CC=CC1=CC=CC=C1O WHGXZPQWZJUGEP-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical group CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000220259 Raphanus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 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
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JDVIRCVIXCMTPU-UHFFFAOYSA-N ethanamine;trifluoroborane Chemical compound CCN.FB(F)F JDVIRCVIXCMTPU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229960004592 isopropanol Drugs 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
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
Description
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The present invention relates to a novel resin composition useful for adhesives, paints, laminated materials, molding materials, and the like. Conventionally, epoxy resins have been widely used for the above-mentioned purposes, but although these resins have various excellent properties, they have insufficient heat resistance. On the other hand, products with excellent heat resistance are made by further prepolymerizing a dicyanate compound produced by the reaction of bisphenol A and chlorocyan, for example.
A triazine-based resin called Triazine A is known, and although this resin has various excellent properties in addition to heat resistance, the cyanate group present in the resin is easily hydrolyzed, resulting in poor storage stability. It had the disadvantage of being inferior. For this reason, the present inventors have conducted intensive studies to develop a curable resin composition that has properties equivalent to or better than triazine resins and also has excellent storage stability. The inventors discovered that a triazine resin obtained from propenylphenol and s-triazine trihalide not only has excellent physical properties but also excellent storage stability, leading to the present invention. That is, the present invention includes a polymerizable unsaturated compound obtained by reacting m-isopropenylphenol and s-triazine trihalide in the presence of a base at a molar ratio of 3:0.8 to 1.2 and a curing catalyst. It is a curable resin composition. The polymerizable unsaturated compound used in the present invention is obtained by the reaction of m-isopropenylphenol and s-triazine trihalide, such as s-triazine trichloride, and
As shown in the structural formula below, it has a triazine skeleton in the molecule. In the reaction between m-isopropenylphenol and s-triazine trihalide, the reaction molar ratio is usually 3:0.8 to 1.2, and since this reaction is a dehydrohalogenation reaction, the amount of hydrogen halide produced is removed. Therefore, it is necessary to have about 1 mol of base present in the reaction system per 1 mol of by-produced hydrogen halide. Such bases include, for example, alkali metal hydroxides such as sodium or potassium hydroxide, alkali metal carbonates such as sodium or potassium carbonate, alcoholates such as sodium methylate or potassium tertiary butyrate, or triethylamine, diethyl Tertiary amines such as aniline and pyridine. The reaction is usually carried out in a solution or suspension system, and suitable reaction solvents for such reactions include, for example, lower aliphatic alcohols such as methanol, ethanol, n-propanol or iso-propanol, acetone, methyl ethyl ketone,
aliphatic ketones such as diethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone, aliphatic hydrocarbons, which are the fractions that accumulate during distillation of natural product mixtures such as petroleum ether, light petrol or petrol; Hydrogen, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, perchloroethylene, chlorobenzene, dichlorobenzene, ethers such as diethyl ether or diisopropyl ether, nitromethane, nitrobenzene. Examples include nitrohydrocarbons such as nitrotoluene, and water. The reaction is usually carried out at a temperature of 0 to 100°C, preferably 70°C or lower. The reaction mixture obtained by such a reaction can be prepared according to a known method, for example, when an organic solvent is used as the reaction solvent, water is added to the reaction mixture to dissolve the by-produced hydrohalide salt in water. After separating the aqueous solution, the desired polymerizable unsaturated compound is obtained by removing the solvent by distillation or the like. Of course, this treatment is not limited to the above method, and any method may be selected depending on the respective manufacturing conditions. The polymerizable unsaturated compound thus obtained can be polymerized by mere heating, but it is thought that it can be polymerized more effectively by using a curing catalyst to form a polymer having an indane structure. . The curable resin composition of the present invention is a resin composition containing such a polymerizable unsaturated compound and a curing catalyst, and the composition has not only excellent storage stability but also excellent heat resistance. The cured product exhibits a variety of excellent properties. Examples of curing catalysts used here include organic acids such as p-toluenesulfonic acid, salicylic acid, acetic acid, and maleic acid; acid anhydrides such as maleic anhydride, methylnadic anhydride, phthalic anhydride, and methyltetrahydrophthalic acid; and hydrochloric acid. Examples include mineral acids such as phosphoric acid and sulfuric acid, Lewis acids such as BF 3 -monoethylamine, aluminum chloride, and metal salts of organic acids, imidazole and its derivatives. In the present invention, the amount of the curing catalyst to be used is not particularly limited, and is appropriately set depending on the type of catalyst used and the type and amount of the combined resin described below. In the curable resin composition of the present invention, various compounds can be added depending on the purpose and use, but in particular m-isopropenyl phenyl glycidyl ether or furthermore two or more epoxy compounds in the molecule. By adding and blending an epoxy compound having a group, the resulting curable resin composition also has the excellent properties of an epoxy resin, and exhibits extremely excellent performance. In this case, the mixing ratio of the polymerizable unsaturated compound and m-isopropenylphenyl glycidyl ether is:
Usually, the weight ratio is 5-100:0-95, and m
- The mixing ratio of isopropenyl phenyl glycidyl ether and epoxy compound is usually 5 to 5 by weight.
The ratio is more preferably 20-100:0-80 than 100:5-95. Examples of such epoxy compounds include bisphenol A-based epoxy resins, resorcinol-based epoxy resins, cresol novolak-type epoxy resins, diglycidyl ether of polyethylene glycol, and meta-aminophenol-based epoxy resins. Furthermore, the curable resin composition of the present invention may contain various natural, semi-synthetic, or synthetic resins in order to improve the properties of the resin in the final coating film, adhesive layer, molded product, etc. can. Such resins include oleoresins such as drying oils and semi-drying oils, rosins, Sierraks, Kobals, oil-modified rosins, phenolic resins, alkyd resins, urea resins, melamine resins, polyester resins, unsaturated polyester resins, and epoxy acrylates. , vinyl butyral resin, vinyl acetate resin,
One type or a combination of two or more of vinyl chloride resins, acrylic resins, and silicone resins can be mentioned, and these resins can be used within a range that does not impair the original properties of the curable resin composition of the present invention, such as the total resin amount. of 30
It can be blended in an amount of less than % by weight. In addition, carbon fiber, glass fiber, alumina fiber,
Alternatively, organic fibers such as nylon and polyester, reinforcing materials and fillers such as calcium carbonate, alumina, kaolin, diatomaceous earth, glass powder, finely powdered silica, and graphite can be used. Although these reinforcing materials and fillers vary depending on the application, they can be used in amounts up to about 4 times the weight per solid resin content for laminated materials and molding materials.
Further, for the purpose of coloring, pigments and dyes such as titanium dioxide, yellow lead, carbon black, red iron oxide, red radish, and silver oxide can be contained. Furthermore, when the resin composition of the present invention is used for paint purposes, it may be used as a coloring dye, a rust preventive pigment, an anti-sagging agent, a dispersant, a thickener, a paint film modifier, an extender pigment, a flame retardant, etc. It can contain paint formulations that are well known per se. The curable resin composition of the present invention may exist in any form such as a solid solution or a dispersion. For example, the above ingredients may be dissolved in ketones such as methyl ethyl ketone, esters such as ethyl acetate, methyl methacrylate, ethers such as dibutyl ether, aromatic hydrocarbons such as toluene, xylene, styrene, dimethylstyrene, or mixtures thereof. It can be used after being dispersed. It is also possible to add an emulsifier and use it as an aqueous dispersion. Furthermore, it can be used for various purposes in the form of a dry powder, pellet, impregnated product, compound, or the like. When using the curable resin composition of the present invention, the temperature required for curing depends on the type of catalyst,
It varies depending on the amount used, etc., but generally 70â to 250â
Preferably it is in the range of 100°C to 200°C. The required heating time varies considerably depending on the conditions of use, such as whether the resin composition is a thin coating, a relatively thick molded product, or a laminate, but generally speaking, it is 30 seconds. ~10 hours, and a time sufficient for the resin component to be completely cured may be selected depending on each usage condition. Molded products using the resin composition of the present invention,
When used in the production of laminated products or adhesive structures, it is generally desirable to apply a pressure of 10 to 100 kg/cm 2 during curing. The present invention will be explained below using examples. However, in the examples, parts mean parts by weight. Reference example 1 s-triazine trichloride 184g (1 mol)
was dissolved in acetone 2.5. A dispersion of 402 g (3 mol) of m-isopropenylphenol and 120 g (3 mol) of caustic soda dispersed in 500 ml of distilled water was added dropwise to this at 20°C, and then the mixture was kept at 50°C for 1 hour to react. I did this. After the reaction is complete, the reaction mixture is distilled to remove acetone, then 50% of water is added to dissolve the sodium chloride produced during the reaction, the crystals are taken out by filtration, washed with water, and dried to obtain the target compound (compound A). ) was obtained. Yield: 463 g (yield: 97%) Example 1 Compound A obtained in Reference Example 1 was dissolved in methyl ethyl ketone to prepare a varnish with a solid content of 70% by weight.
A resin composition was prepared by adding 1 part of boron trifluoride-monoethylamine to 100 parts of this varnish. After impregnating a plain weave glass cloth with the resin composition, the solvent was removed. This was air-dried at room temperature until there was no tack, and then dried at 120-130°C for 7 minutes to B-stage the impregnated resin. The obtained prepreg and copper foil were layered and heated at 180â for 2 hours.
The copper-clad laminate was then cured using a hot press at 190° C. for 2 hours to obtain a copper-clad laminate. The properties of the obtained laminate (according to the test method specified in JIS C-6481) are shown in Table 1. Comparative Example 1 KU-6573 (a triazine resin derived from 2,2-bis(4-cyanatophenyl)propane, a varnish with a solid content of 70% by weight using methyl ethyl ketone as a solvent. A Bayer product) 8% in 143 parts A resin composition was prepared by mixing 0.2 part of zinc octylate, 0.1 part of catechol, and 0.075 part of 2-ethyl-4-methylimidazole. After impregnating a plain weave glass cloth with the resin composition, the solvent was removed. This was air-dried at room temperature until there was no tack, and then dried at 125-140°C for 7 minutes to B-stage the impregnated resin. The obtained prepreg and copper foil were layered and heated at 180â for 2 hours.
The copper-clad laminate was then cured using a hot press at 190° C. for 2 hours to obtain a copper-clad laminate. Table 1 shows the properties of the obtained laminate. Comparative Example 2 100 parts of Sumiepoxy ESCN-220L (cresol novolak type epoxy resin, trade name of Sumitomo Chemical Co., Ltd.) was dissolved in 43 parts of methyl ethyl ketone, and then Sumikiure-M (4,4'-diaminodiphenylmethane, trade name of Sumitomo Chemical Co., Ltd.) was dissolved. ) was added and uniformly dissolved to prepare a resin composition. Thereafter, a laminate was obtained in the same manner as in Comparative Example 2. Table 1 shows the properties of the obtained laminate. Example 2 Compound A obtained in Reference Example 1 was left in an atmosphere of 40°C and 100% relative humidity for one week, and then
A laminate was produced in the same manner as in Example 1. The properties of the obtained laminate are shown in Table 1, and the properties are almost the same as in Example 1, and even when Compound A was stored under high humidity as described above, no effect was observed. Ta. Comparative Example 3 KU-6573 (described above) was left in an atmosphere of 40° C. and 100% relative humidity for one week, and then a laminate was prepared in the same manner as in Comparative Example 1. The properties of the obtained laminate are shown in Table 1, and the properties were extremely poor, and the influence of humidity during storage of the raw resin was very large. Example 3 After mixing 50 parts of m-isopropenyl phenyl glycidyl ether with 50 parts of the compound A obtained in Reference Example 1,
It was heated to 120°C to uniformly dissolve it. After lowering the temperature to 80°C, 2 parts of 2-ethyl-4-methylimidazole and 45 parts of methylnadic anhydride are added,
The mixture was thoroughly stirred to obtain a resin composition. This resin composition was injected into a casting mold made by sandwiching a 3 mm thick silicone rubber spacer between two glass plates, and held at 120°C for 2 hours, 150°C for 1 hour, and 180°C for 1 hour to stage cure. I did it. The properties of the obtained cast plate are shown in Table 2. Comparative Example 4 2 parts of 2-ethyl-4-methylimidazole and 90 parts of methylnadic anhydride were added to 100 parts of Sumiepoxy ELA-128 (bisphenol-based epoxy resin, manufactured by Sumitomo Chemical Co., Ltd.), and the mixture was stirred well at 80°C to form a resin. A composition was obtained. A cast plate was made using the resin composition in the same manner as in Example 3. The properties of the obtained cast plate are shown in Table 2. Example 4 50 parts of the compound A obtained in Reference Example 1, 10 parts of m-isopropenyl phenyl glycidyl ether, 20 parts of Sumiepoxy ESA-014 (bisphenol solid epoxy resin, softening point 95-104°C, Sumitomo Chemical Co., Ltd.) ,
Sumiepoxy ESA-017 (bisphenol solid epoxy resin, softening point 122-131â, Sumitomo Chemical Co., Ltd. product) 20 parts, dicyandiamide 2 parts, 2-ethyl-
After roll mixing 2 parts of 4-methylimidazole, 50 parts of titanium oxide and 1 part of Erosil, 150Ό
It was ground to the following particle size. Powder coating using this powder (-70KV charging)
The film was baked at 150°C for 1 hour and then at 1180°C for an additional 1 hour. Table 3 shows the performance of the resulting coating film. Comparative Example 5 Powder coating was carried out in exactly the same manner as in Example 4, except that Sumiepoxy ESA-014 was used instead of Compound A. The performance of the obtained coating film is shown below.
Shown in 3.
ãè¡šããtableã
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Claims (1)
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èçµæç©ã[Claims] 1. A polymerizable unsaturated compound obtained by reacting m-isopropenylphenol and s-triazine trihalide in the presence of a base at a molar ratio of 3:0.8 to 1.2 and a curing catalyst. A curable resin composition containing. 2 A polymerizable unsaturated compound and m-isopropenyl phenyl glycidyl ether obtained by reacting m-isopropenylphenol and s-triazine trihalide in the presence of a base at a molar ratio of 3:0.8 to 1.2. and a curable resin composition containing a curing catalyst. 3 Polymerizable unsaturated compound and m-isopropenyl phenyl glycidyl ether obtained by reacting m-isopropenylphenol and s-triazine trihalide in the presence of a base at a molar ratio of 3:0.8 to 1.2. A curable resin composition containing an epoxy compound having two or more epoxy groups in the molecule and a curing catalyst.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8087779A JPS564610A (en) | 1979-06-26 | 1979-06-26 | Curable resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8087779A JPS564610A (en) | 1979-06-26 | 1979-06-26 | Curable resin composition |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP769786A Division JPS61210077A (en) | 1986-01-16 | 1986-01-16 | S-triazine-containing compound |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS564610A JPS564610A (en) | 1981-01-19 |
JPS6244564B2 true JPS6244564B2 (en) | 1987-09-21 |
Family
ID=13730569
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8087779A Granted JPS564610A (en) | 1979-06-26 | 1979-06-26 | Curable resin composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS564610A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04156066A (en) * | 1990-10-19 | 1992-05-28 | Erubetsukusu Video Kk | Method and device for converting synchronizing signal |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0696613B2 (en) * | 1986-02-25 | 1994-11-30 | äœåååŠå·¥æ¥æ ªåŒäŒç€Ÿ | Reactive polymer manufacturing method |
US4808717A (en) * | 1986-09-17 | 1989-02-28 | Sumitomo Chemical Company, Limited | Thermosetting resin composition |
JPH0776377B2 (en) * | 1987-03-11 | 1995-08-16 | æ°æ¥æ¬è£œéµæ ªåŒäŒç€Ÿ | Manufacturing method of high strength steel plate with excellent low temperature toughness |
WO2024143964A1 (en) * | 2022-12-28 | 2024-07-04 | ìœì€ë¡±ìžëì€ížëŠ¬ 죌ìíì¬ | Curing agent composition and curable composition containing same |
-
1979
- 1979-06-26 JP JP8087779A patent/JPS564610A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04156066A (en) * | 1990-10-19 | 1992-05-28 | Erubetsukusu Video Kk | Method and device for converting synchronizing signal |
Also Published As
Publication number | Publication date |
---|---|
JPS564610A (en) | 1981-01-19 |
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