JPH0485323A - Thermosetting resin composition - Google Patents
Thermosetting resin compositionInfo
- Publication number
- JPH0485323A JPH0485323A JP20081790A JP20081790A JPH0485323A JP H0485323 A JPH0485323 A JP H0485323A JP 20081790 A JP20081790 A JP 20081790A JP 20081790 A JP20081790 A JP 20081790A JP H0485323 A JPH0485323 A JP H0485323A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- acid
- meth
- compound
- composition
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 14
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 10
- 239000003822 epoxy resin Substances 0.000 claims abstract description 42
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000002245 particle Substances 0.000 claims abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 12
- 230000005484 gravity Effects 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract description 3
- 239000006185 dispersion Substances 0.000 abstract description 3
- 238000010107 reaction injection moulding Methods 0.000 abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 abstract 1
- -1 amine phenols Chemical class 0.000 description 32
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 229920000768 polyamine Polymers 0.000 description 13
- 229920005862 polyol Polymers 0.000 description 12
- 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 10
- 150000003077 polyols Chemical class 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000005263 alkylenediamine group Chemical group 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical class C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-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
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 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 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明はエポキシ樹脂系有機フィラーを含有した成形性
の良好な熱硬化性樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a thermosetting resin composition containing an epoxy resin organic filler and having good moldability.
[従来の技術]
従来、多官能(メタ)アクリレートを硬化させてフィル
ム、塗膜、成形品等を製造する際フィラー等を添加して
硬化収縮を押さえる方法が知られている。[Prior Art] Conventionally, a method is known in which a filler or the like is added to suppress curing shrinkage when polyfunctional (meth)acrylate is cured to produce films, coatings, molded products, etc.
[発明が解決しようとする課題]
しかしながら従来のフィラー等をもちいると、分散後の
安定性が悪い、比重が大きい等の問題点があった。[Problems to be Solved by the Invention] However, when conventional fillers and the like are used, there are problems such as poor stability after dispersion and high specific gravity.
[課題を解決するための手段]
本発明者らは、かかる問題点なく、硬化収縮を押さえる
熱硬化性樹脂組成物を得るべく鋭意検討した結果、本発
明に到達した。[Means for Solving the Problems] The present inventors have arrived at the present invention as a result of intensive studies to obtain a thermosetting resin composition that suppresses curing shrinkage without such problems.
すなわち、本発明は1分子中に少なくとも1個の(メタ
)アクリル性不飽和結合を有する化合物(a)中に分散
されたエポキシ樹脂硬化物の粒子(b)を含むことを特
徴とする熱硬化性樹脂組成物(本発明の化合物と略記)
であり、とくに(a)中でエポキシ樹脂を硬化剤および
/または硬化触媒と反応させてエポキシ樹脂硬化物粒子
を生成させることにより得られる熱硬化性樹脂組成物で
ある。That is, the present invention provides a thermosetting method characterized by containing particles (b) of a cured epoxy resin dispersed in a compound (a) having at least one (meth)acrylic unsaturated bond in one molecule. Resin composition (abbreviated as compound of the present invention)
In particular, it is a thermosetting resin composition obtained by reacting an epoxy resin with a curing agent and/or a curing catalyst in (a) to produce cured epoxy resin particles.
本発明に使用できるエポキシ樹脂としては、通常のもの
、たとえば「新エポキシ樹脂」 [垣内弘著、(株)昭
晃堂、昭和60年5月10日発行] 15〜97頁、「
基礎合成樹脂の化学(新版)」[三羽忠広著、技報堂、
昭和50年発行] 371〜392頁、 「エポキシ・
レジンズ」[マグロ−ヒル・ブック・コンパニー社19
57年発行コロ〜29頁に記載のものが使用でき、具体
的には下記のものが挙げられる。Epoxy resins that can be used in the present invention include common ones, such as "New Epoxy Resin" [written by Hiroshi Kakiuchi, published by Shokodo Co., Ltd., May 10, 1985], pp. 15-97, "
Chemistry of Basic Synthetic Resins (New Edition)” [written by Tadahiro Miba, Gihodo,
Published in 1975] pp. 371-392, “Epoxy
Resins” [McGraw-Hill Book Company 19
Those described in 1957, published on page 29 can be used, and specific examples include the following.
(1)フェノールエーテル系エポキシ樹脂[ビスフェノ
ールA型エポキシ樹脂、ビスフェノールF型エポキシ樹
脂、ビスフェノールAD型エポキシ樹脂、ハロゲン化ビ
スフェノールA型エポキシ樹脂、フェノールノボラック
型エポキシ樹脂、タレゾールノボラック型エポキシ樹脂
、ハロゲン化フェノールノボラック型エポキシ樹脂など
コ;(2)エーテル系エポキシ樹脂[ポリオール、ポリ
エーテルポリオール、などとエピクロルヒドリンとの縮
合物など];(3)エステル系エポキシ樹脂[グリシジ
ル(メタ)アクリレートとエチレン性不飽和単量体(ア
クリロニトリルなど)との共重合体などコ;(4)グリ
シジルアミン系エポキシ樹脂[たとえばアニリン、ジア
ミノジフェニルメタン、アミンフェノール類、キシリレ
ンジアミン、ハロゲン化アニリン、ビスアミノメチルシ
クロヘキサンなどのアミン類とエピクロルヒドリンとの
縮合物なとコ;(5)非グリシジル型エポキシ樹脂[環
状エポキシ樹脂、エボキン化ポリブタジェン、エポキシ
化大豆油など]:およびこれらの2種以上の混合物。(1) Phenol ether type epoxy resin [bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD type epoxy resin, halogenated bisphenol A type epoxy resin, phenol novolac type epoxy resin, Talezol novolac type epoxy resin, halogenated (2) Ether-based epoxy resins [condensates of polyols, polyether polyols, etc. and epichlorohydrin, etc.]; (3) Ester-based epoxy resins [glycidyl (meth)acrylate and ethylenically unsaturated Copolymers with monomers (such as acrylonitrile); (4) glycidylamine-based epoxy resins [e.g., amines such as aniline, diaminodiphenylmethane, amine phenols, xylylene diamine, halogenated aniline, and bisaminomethylcyclohexane; and epichlorohydrin; (5) non-glycidyl epoxy resins [cyclic epoxy resins, evoquinated polybutadiene, epoxidized soybean oil, etc.]; and mixtures of two or more of these.
エポキシ樹脂のうち好ましいものはフェノールエーテル
系エポキシ樹脂およびグリシジルアジン系エポキシ樹脂
である。Among the epoxy resins, preferred are phenol ether epoxy resins and glycidyl azine epoxy resins.
本発明において、エポキシ樹脂との反応に使用できる硬
化剤としては、ポリアミン、ポリカルボン酸とその無水
物などがある。In the present invention, curing agents that can be used in the reaction with the epoxy resin include polyamines, polycarboxylic acids, and their anhydrides.
ポリアミンの具体例としては、(1)脂肪族ポリアミン
類、たとえばエチレンジアミン、テトラメチレンレンジ
アミン、ヘキサメチレンジアミンなどのアルキレンジア
ミン、ジエチレントリアミン、イミノビスプロピルアミ
ン、ビス(ヘキサメチレン) ト リアミ ン、 ト
リエチレンテ トラ ジン、 テトラエチレンペンタミ
ン、ペンタエチレンヘキサミンなどのポリアルキレン(
アルキレンの炭素数2〜6)ポリアミン、アルキル(炭
素数1〜3)アミノプロピルアミン、アミノエチルエタ
ノールアミン、メチルイミノビスプロピルアミンなどの
アルキル(炭素数1〜4)またはヒドロキンアルキル(
アルキルの炭素数2〜4)アミン化合物、キシリレンジ
アミン、テトラクロル−p−キンリレンジアミンなどの
芳香環含有脂肪族アミン類、ポリオキシテトラメチレン
ポリアミン、ポリオキシプロピレンポリアミンなどのポ
リエーテルポリアミン類など、(2)脂環または複素環
含有脂肪族ポリアミン、たとえば、メンタンジアミン、
N−アミノエチルピペラジン、I、3−ジアミノシクロ
ヘキサン、インホロンジアミン、水添メチレンジアニリ
ン、3.9−ビス(3−アミノプロピル)−2,4,8
,10−テトラオキサスピロ[5,5コウンデカンなど
、(3)芳香族ポリアミンたとえば、フェニレンジアミ
ン、 トルエンジアミン、ジアミノジフェニルメタン、
ジアミノジフェニルスルホン、ベンジジン、4.4’−
ビス(0−トルイジン)、チオジアニリン、ジアニシジ
ン、メチレンビス(0−クロロアニリン)、ビス(3,
4−ジアミノフェニル)スルホン、ジアミノジトリルス
ルホン、2,6−ジアミツピリジン、4−クロロO−フ
ェニレンジアミン、4−メトキン−6−メチル−mフェ
ニレンジアミン、m−アミノベンジルアミン、4.4′
−ジアミノ−3,3′−ジメチルジフェニルメタンなと
、(4)ポリアミドポリアミン(上記ポリアミン類とダ
イマー酸との縮合物)(5)ベンゾグアナミンおよび/
またはアルキルグアナミンおよびその変性物、および(
6)ジンアンジアミドなどが挙げられる。Specific examples of polyamines include (1) aliphatic polyamines, such as alkylene diamines such as ethylene diamine, tetramethylene diamine, and hexamethylene diamine, diethylene triamine, iminobispropylamine, bis(hexamethylene) triamine, and triamine;
Polyalkylenes (such as polyethylenetetrazine, tetraethylenepentamine, and pentaethylenehexamine)
alkylene having 2 to 6 carbon atoms) polyamine, alkyl (having 1 to 3 carbon atoms) such as aminopropylamine, aminoethylethanolamine, methyliminobispropylamine, or hydroquine alkyl (having 1 to 4 carbon atoms);
Alkyl having 2 to 4 carbon atoms) amine compounds, aromatic ring-containing aliphatic amines such as xylylene diamine and tetrachloro-p-quinlylene diamine, polyether polyamines such as polyoxytetramethylene polyamine and polyoxypropylene polyamine, etc. (2) Alicyclic or heterocyclic-containing aliphatic polyamines, such as menthanediamine,
N-aminoethylpiperazine, I,3-diaminocyclohexane, inphoronediamine, hydrogenated methylene dianiline, 3,9-bis(3-aminopropyl)-2,4,8
, 10-tetraoxaspiro[5,5-oundecane, etc.; (3) Aromatic polyamines such as phenylenediamine, toluenediamine, diaminodiphenylmethane,
Diaminodiphenylsulfone, benzidine, 4.4'-
Bis(0-toluidine), thiodianiline, dianisidine, methylenebis(0-chloroaniline), bis(3,
4-diaminophenyl) sulfone, diaminoditolylsulfone, 2,6-diamitupyridine, 4-chloroO-phenylenediamine, 4-methquine-6-methyl-m-phenylenediamine, m-aminobenzylamine, 4.4'
-diamino-3,3'-dimethyldiphenylmethane, (4) polyamide polyamine (condensate of the above polyamines and dimer acid), (5) benzoguanamine and/
or alkylguanamine and its modified products, and (
6) Examples include diandiamide.
ポリカルボン酸およびその無本物の具体例トしては、コ
ハク酸、マレイン酸、イタコン酸、アゼライン酸、セパ
チン酸、フタル酸、テトラヒドロフタル酸、メチルテト
ラヒドロフタル酸、ヘキサヒドロフタル酸、ナジック酸
、メチルナンック酸、ドデセニルコハク酸、ピロメリッ
ト酸、 トリメリット酸、クロレンディック酸、メロフ
ァ二酸、ベンゾフェノンテトラカルボン酸、シクロペン
タジェンテトラカルボン酸、フェニレンビス(3−ブタ
ン−1,2−ジカルボン酸などおよびこれらの無水物が
あげられる。Specific examples of polycarboxylic acids and their non-authentic properties include succinic acid, maleic acid, itaconic acid, azelaic acid, sepacic acid, phthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, nadic acid, Methylnanucic acid, dodecenylsuccinic acid, pyromellitic acid, trimellitic acid, chlorendic acid, merofadiic acid, benzophenonetetracarboxylic acid, cyclopentadienetetracarboxylic acid, phenylenebis(3-butane-1,2-dicarboxylic acid, etc.) Examples include these anhydrides.
硬化剤とともに、または硬化剤に変えてエボキシ硬化触
媒を使用することができる。硬化触媒の具体例としては
、(1)3級アミン類、たとえば、ピリジン、キノリン
、イミダゾール、N、N−ンメチルシクロヘキシルアミ
ン、 トリエチルアミン、N−メチルモルホリン、N−
エチルモルホリン、 トリエチレンジアミン、N、N−
ンメチルアミリン、N、N−ジメチルベンジルアミン、
トリス(N、N−ジメチルアミンメチル)フェノール
など、(2)第4級アンモニウム化合物、たとえば、テ
トラメチルアンモニウムクロライド、テトラメチルアン
モニウムブロマイド、トリメチルベンジルアンモニウム
クロライド、テトラメチルアンモニウムヒドロキンドな
ど、(3)塩基性アルカリ金属化合物、たとえば、ソジ
ウムメトキンド、苛性カリ、2−エチルヘキサン酸カリ
ウムなと、(4)金属ハロゲン化物、たとえば、5nC
14、FeCl3、AlCl3.5bC16、BF3、
ZnCl2、ZnBr2、Kl、 LICIなど(5
)有機金属化合物、たとえば、トリエチルアルミニウム
、アルムニウムイソプロボキシド、テトライソプロピル
チタネート、ジエチル亜鉛、n−ブトキシリチウム、酢
酸亜鉛、2−エチルヘキサン酸鉛、アセチルアセトネー
ト化合物(Fe。Epoxy curing catalysts can be used with or in place of the curing agent. Specific examples of curing catalysts include (1) tertiary amines, such as pyridine, quinoline, imidazole, N,N-methylcyclohexylamine, triethylamine, N-methylmorpholine, N-
Ethylmorpholine, triethylenediamine, N, N-
N-methylamyline, N,N-dimethylbenzylamine,
(2) quaternary ammonium compounds, such as tetramethylammonium chloride, tetramethylammonium bromide, trimethylbenzylammonium chloride, tetramethylammonium hydroquine, etc., (3) bases, such as tris(N,N-dimethylaminemethyl)phenol; and (4) metal halides, such as 5nC.
14, FeCl3, AlCl3.5bC16, BF3,
ZnCl2, ZnBr2, Kl, LICI, etc. (5
) Organometallic compounds such as triethylaluminum, aluminum isoproboxide, tetraisopropyltitanate, diethylzinc, n-butoxylithium, zinc acetate, lead 2-ethylhexanoate, acetylacetonate compounds (Fe.
co)など、(6)リン系化合物、たとえば、 トリア
ルキルフォスフイン、 トリアルキルフォスフインオキ
ノド、フォスフオニウム塩など、(7)硼素化合物、た
とえば、 トリアルキル−1トリアリール−またはトリ
シクロアルキルボレートなど、などが挙げられる。co), (6) phosphorus compounds, such as trialkylphosphine, trialkylphosphine oquinide, phosphonium salts, etc., (7) boron compounds, such as trialkyl-1-triaryl- or tricycloalkyl. Examples include borate, etc.
本発明において使用される1分子中に少なくとも1個の
(メタ)アクリル性不飽和結合を有する化合物としては
、1分子中に少なくとも1個の水酸基を有する化合物の
(メタ)、アクリル酸エステルおよび1分子中に少なく
とも1個の水酸基を有する化合物にヒドロキシアルキル
(メタ)アクリレートをジイソシアネートによるウレタ
ン結合を介して導入したいわゆるウレタン(メタ)アク
リレートなどがあげられる。これらの1分子中に少なく
とも1個の(メタ)アクリル性不飽和結合ををする化合
物の原料となる、1分子中に少なくとも1個の水酸基を
有する化合物の具体例としては、水酸基当量30〜20
,000で1分子当たりの平均官能基数が1〜8である
水酸基を有する化合物、たとえば低分子量の脂肪族1価
および多価アルコール(脂環、芳香環およびヘテロ環を
有するものを含む)ポリエーテルポリオール、ポリエス
テルポリオール、ポリジエン系ポリオールおよびその水
添化物ならびにアクリルポリオールからなる群より選ば
れる1種または2種以上の混合物などがあげられる。Compounds having at least one (meth)acrylic unsaturated bond in one molecule used in the present invention include (meth)acrylic esters and acrylic esters of compounds having at least one hydroxyl group in one molecule. Examples include so-called urethane (meth)acrylates in which a hydroxyalkyl (meth)acrylate is introduced into a compound having at least one hydroxyl group in the molecule through a urethane bond formed by a diisocyanate. Specific examples of compounds having at least one hydroxyl group in one molecule, which are raw materials for these compounds having at least one (meth)acrylic unsaturated bond in one molecule, include those having a hydroxyl equivalent of 30 to 20.
,000 and the average number of functional groups per molecule is 1 to 8, such as low molecular weight aliphatic monohydric and polyhydric alcohols (including those having alicyclic rings, aromatic rings, and heterocycles) polyethers. Examples include one or a mixture of two or more selected from the group consisting of polyols, polyester polyols, polydiene polyols and hydrogenated products thereof, and acrylic polyols.
1価および多価アルコールの具体例としては、オクチル
アルコール、2−エチルヘキサノール、ラウリルアルコ
ール、ステアリルアルコール、オレイルアルコール、シ
クロヘキサノール、ベンノルアルコールなどの1価アル
コール(炭素数6〜20);エチレングリコール、プロ
ピレングリコール、114−ブタンジオール、1,3−
ブタンジオール、ネオペンチルグリコール、l、6−ヘ
キサンジオールなどのアルキレングリコール(炭素数2
〜6)、シクロヘキサンジオール、シクロヘキサンジメ
タツール等の脂環式グリコール類; グリセリン、 ト
リメチロールプロパン、トリメチロールエタン、ヘキサ
ントリオール、 ペンタエリスリ トール、 ジグリセ
リン、α−メチルグルコ/ド、ソルビトール、キノリッ
ト、マンニット、グルコース、フラクトース、蔗糖等の
3〜8価のアルコールなどがあげられる。Specific examples of monohydric and polyhydric alcohols include monohydric alcohols (with 6 to 20 carbon atoms) such as octyl alcohol, 2-ethylhexanol, lauryl alcohol, stearyl alcohol, oleyl alcohol, cyclohexanol, and bennor alcohol; ethylene glycol; , propylene glycol, 114-butanediol, 1,3-
Alkylene glycols (with 2 carbon atoms) such as butanediol, neopentyl glycol, l,6-hexanediol, etc.
~6), alicyclic glycols such as cyclohexanediol and cyclohexane dimetatool; glycerin, trimethylolpropane, trimethylolethane, hexanetriol, pentaerythritol, diglycerin, α-methylgluco/de, sorbitol, quinolite, mannitol , tri- to octavalent alcohols such as glucose, fructose, and sucrose.
ポリエーテルポリオールとしては、活性水素原子含有化
合物[OR,N H2、NH,Coonなどの活性水素
原子含打基を仔する化合物、たとえばアルコール類、フ
ェノール類、アミン類、燐酸類、カルホン酸類コにアル
キレンオキサイドを付加して得られる、分子中に1個ま
たは2個以上の水酸基を仔するポリエーテル[ポリエー
テルモノオールおよびポリエーテルモノオールコが挙げ
られる。Polyether polyols include active hydrogen atom-containing compounds [compounds containing active hydrogen atom-impregnated groups such as OR, NH2, NH, Coon, etc., such as alcohols, phenols, amines, phosphoric acids, and carbonic acids; Polyethers having one or more hydroxyl groups in the molecule, which are obtained by adding alkylene oxide, include polyether monools and polyether monools.
上記ポリエーテルの製造に用いられる活性水素原子含有
化合物としては
(1)メタノール、エタノール、プロパツール、ブタノ
ール、ペンタノール、ヘキサノールなどの他上記1価お
よび多価アルコールの具体例であげたち(7); (
2)フェノール類、たとえば: フェノール、モノ−ま
たはジ−アルキル(炭素数1〜20)フェノール(クレ
ゾール、ジノニルフェノールなト)、ナフトールなどの
1価フェノール類;ハイドロキノン、カテコール、レゾ
ルンン、ピロガロール、ビスフェノール類(ビスフェノ
ールA1 ビスフェノールスルフォン、ビスフェノー
ルFなど)、フェノール−ホルムアルデヒド縮合物(ノ
ボラック樹脂、レゾール樹脂の中間物)等の多価フェノ
ール類;(3)脂肪族、脂環式、芳香族および複素環式
の、モノ−およびポリアミン類、たとえば;アンモニア
; モノ、ジーおよびトリーのエタノールおよび/また
はプロパツールアミンなどのアルカノールアミン類;モ
ノ−およびジ−アルキル(炭素数1〜20)アミン、ア
ルキレンジアミン(炭素数2〜6)(エチレンジアミン
、ヘキサメチレンジアミンなど)、ポリアルキレン(炭
素数2〜6)ポリアミン(ジエチレントリアミン、 ト
リエチレンテトラミンなど)等の脂肪族アミン;アニリ
ン、フェニレンジアミン、ジアミノトルエン、キシリレ
ンジアミン、メチレンジアニリン、ジエチルトリレンジ
アミン、ジフェニルエーテルジアミンなどの芳香族アミ
ン類;インホロンジアミン、ジシクロヘキシルメタンジ
アミンなどの脂環式アミン類; ピペラジン、アミノエ
チルピペラジン、その他特公昭55−21044号公報
記載の複素環式アミン類など;
(4)脂肪族、脂環式および芳香族の、飽和および不飽
和の、1価および多価カルボン酸、たとえば;酢酸、プ
ロピオン酸、酪酸、オクタン酸、ラウリン酸、ステアリ
ン酸、オレイン酸、安息香酸などのモノカルボン酸(炭
素数1〜20); アジピン酸、フタル酸などのジカル
ボン酸等;
(5)燐酸類、たとえば;正燐酸、メタ燐酸、ピロ燐酸
、ポリ燐酸、亜燐酸など;およびこれらの酸性エステル
(ジブチルピロ燐酸など)等;およびこれらの2種以上
の混合物が挙げられる。Examples of active hydrogen atom-containing compounds used in the production of the above polyether include (1) methanol, ethanol, propatool, butanol, pentanol, hexanol, and other specific examples of the monohydric and polyhydric alcohols mentioned above (7) ; (
2) Phenols, for example: Monohydric phenols such as phenol, mono- or di-alkyl (1 to 20 carbon atoms) phenol (cresol, dinonylphenol, etc.), naphthol; hydroquinone, catechol, resolun, pyrogallol, bisphenols. (bisphenol A1, bisphenol sulfone, bisphenol F, etc.), polyhydric phenols such as phenol-formaldehyde condensates (novolak resin, resol resin intermediate); (3) aliphatic, alicyclic, aromatic and heterocyclic , mono- and polyamines, such as; ammonia; alkanolamines such as mono-, di- and tri-ethanol and/or propatoolamines; mono- and di-alkyl (1 to 20 carbon atoms) amines, alkylene diamines (carbon atoms 2-6) Aliphatic amines such as (ethylenediamine, hexamethylenediamine, etc.), polyalkylene (carbon number 2-6) polyamines (diethylenetriamine, triethylenetetramine, etc.); aniline, phenylenediamine, diaminotoluene, xylylenediamine, methylene Aromatic amines such as dianiline, diethyltolylene diamine, and diphenyl ether diamine; Alicyclic amines such as inphorone diamine and dicyclohexylmethane diamine; Piperazine, aminoethyl piperazine, and other heterocycles described in Japanese Patent Publication No. 55-21044 (4) Aliphatic, cycloaliphatic and aromatic, saturated and unsaturated, mono- and polyhydric carboxylic acids, such as acetic acid, propionic acid, butyric acid, octanoic acid, lauric acid, stearic acid. , oleic acid, benzoic acid, and other monocarboxylic acids (1 to 20 carbon atoms); adipic acid, phthalic acid, and other dicarboxylic acids; (5) Phosphoric acids, such as orthophosphoric acid, metaphosphoric acid, pyrophosphoric acid, polyphosphoric acid, Examples include phosphorous acid, etc.; and acidic esters thereof (dibutylpyrophosphoric acid, etc.); and mixtures of two or more thereof.
活性水素含有化合物に付加するアルキレンオキサイドと
しては、エチレンオキサイド(以下EOと略記)、プロ
ピレンオキサイド(以下POと略記)1.2−12.3
−および1.3−ブチレンオキサイド、テトラヒドロフ
ラン、スチレンオキサイド、エピクロルヒドリン等、お
よびこれらの2種以上(たとえばEOとPO)の併用(
ランダムおよび/またはブロック)が挙げられる。Examples of the alkylene oxide added to the active hydrogen-containing compound include ethylene oxide (hereinafter abbreviated as EO) and propylene oxide (hereinafter abbreviated as PO) 1.2-12.3
- and 1,3-butylene oxide, tetrahydrofuran, styrene oxide, epichlorohydrin, etc., and combinations of two or more of these (e.g. EO and PO) (
random and/or block).
ポリエステルポリオールとしては、たとえば、アルキレ
ングリコールC炭素数2〜G) [エチレングリコー
ル、プロピレングリコール、1,4−ブタンジオール、
1,3−ブチレングリコール、ネオペンチルグリコール
、1.トム率サンジオールなどコ、シクロヘキサンジオ
ール、シクロへ牛サンジメタツール等の2価アルコール
の1種または2種以上の混合物、および、マロン酸、琥
珀酸、アジピン酸、マレイン酸、フマル酸、アゼライン
酸、フタル酸、イソフタル酸、テレフタル酸などの2価
カルボン酸およびこれらの無水物の1種または、2種以
上の混合物から合成される末端に水酸基を有する縮合型
ポリエステルポリオールおよび、2価または、3価の低
分子量ポリオールを開始剤とするε−カプロラクトンの
開環重合で得られるポリカプロラクトンポリオールなど
があげられる。Examples of polyester polyols include alkylene glycol (C having 2 to G carbon atoms) [ethylene glycol, propylene glycol, 1,4-butanediol,
1,3-butylene glycol, neopentyl glycol, 1. One or a mixture of two or more dihydric alcohols such as cyclohexane diol, cyclohexane diol, cyclohexane diol, and malonic acid, succinic acid, adipic acid, maleic acid, fumaric acid, and azelaic acid. , phthalic acid, isophthalic acid, terephthalic acid, and other divalent carboxylic acids, and one or a mixture of two or more of these anhydrides. Examples include polycaprolactone polyols obtained by ring-opening polymerization of ε-caprolactone using a low molecular weight polyol as an initiator.
ポリジエン系ポリオールおよびその水添化物としては、
ポリブタジェンポリオール、水添ポリブタジェンポリオ
ール、ポリイソプレンジオール、゛水添ポリイソプレン
ジオールなどがあげられる。As polydiene polyols and their hydrogenated products,
Examples include polybutadiene polyol, hydrogenated polybutadiene polyol, polyisoprene diol, and hydrogenated polyisoprene diol.
アクリルポリオールとしては、メタクリル酸アルキル、
アクリル酸アルキル、スチレン、アクリロニトリルなど
の(メタ)アクリル系モノマーの1種または2種以上と
ヒドロキシエチル(メタ)アクリレートとの共重合物が
あげられる。As the acrylic polyol, alkyl methacrylate,
Examples include copolymers of one or more (meth)acrylic monomers such as alkyl acrylates, styrene, and acrylonitrile and hydroxyethyl (meth)acrylate.
1分子中に少なくとも1個の水酸基を有する化合物に(
メタ)アクリル基を導入して化合物(a)とするには、
1分子中に少なくとも1個の水酸基を有する化合物を(
メタ)アクリル酸でエステル化して(メタ)アクリル酸
エステルとするか、あるいは上記化合物と、ジイソシア
ネートおよびヒドロキシアルキル(メタ)アクリレート
との反応でウレタン(メタ)アクリレートとする方法か
ある。For compounds having at least one hydroxyl group in one molecule (
In order to introduce a meth)acrylic group to obtain compound (a),
A compound having at least one hydroxyl group in one molecule (
There are two methods: esterification with meth)acrylic acid to form a (meth)acrylic acid ester, or reaction of the above compound with a diisocyanate and a hydroxyalkyl (meth)acrylate to form a urethane (meth)acrylate.
ウレタン(メタ)アクリレートを製造する際に用いられ
るジイソシアネートは特に限定はなく、たとえば、炭素
数(NGO基の炭素を除<)6〜20の芳香族ジイソシ
アネート、炭素数2〜18の脂肪族ジイソシアネート、
炭素数4〜15の脂環式ジイソシアネート、炭素数8〜
15の芳香脂肪族ジインシアネート、これらのジイソシ
アネートの変性物(ウレタン基、カルボジイミド基、ア
ロファネート基、ウレア基、オキサゾリン基含有変性物
など)およびこれらジイソシアネートと活性水素含有化
合物からなるウレタンプレポリマーがあげられる。The diisocyanate used in producing urethane (meth)acrylate is not particularly limited, and includes, for example, an aromatic diisocyanate having 6 to 20 carbon atoms (excluding the carbon in the NGO group), an aliphatic diisocyanate having 2 to 18 carbon atoms,
Alicyclic diisocyanate having 4 to 15 carbon atoms, 8 to 15 carbon atoms
Examples include 15 aromatic aliphatic diincyanates, modified products of these diisocyanates (modified products containing urethane groups, carbodiimide groups, allophanate groups, urea groups, oxazoline groups, etc.), and urethane prepolymers made of these diisocyanates and active hydrogen-containing compounds. .
このようなインシアネートとしてはエチレンジインシア
ネート、テトラメチレンジイソシアネート、ヘキサメチ
レンジイソシアネー)(HDI)、ドデカメチレンジイ
ソシアネー)、1,6.II−ウンデカントリイソシア
ネート、2,2.4−)リメチルヘキサンジイソシアネ
ート、リジンジイソシアネート、2.6−ジインシアネ
ートメチルカプロエート、ビス(2−インシアネートエ
チル)フマレート、ビス(2−インシアネートエチル)
カーボネート、2−イソシアネートエチル−2,6−ジ
イツシアネートヘキサノエート;イソホロクジイソシア
ネー)(IPDI)、ジシクロヘキシルメタンジイソシ
アネート(水添MDI)、シクロヘキシレンジイソシア
ネート、メチルシビス(2−イソシアネートエチル)4
−シクロヘキセン1.2−ジカルボキレート;キシリレ
ンジイソシアネート、ジエチルベンゼンジイソシアネー
ト;HDIの水変性物、;トリレンジイソシアネート(
TDI)、粗製TDL ジフェニルメタンジイソシア
ネート(MDI)、変性MDI(カーポジイミド変性M
DIなど)、ナフチレンジイソシアネート;およびこれ
らの2種以上の混合物があげられる。Examples of such incyanates include ethylene diinsyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), dodecamethylene diisocyanate), 1,6. II-undecane triisocyanate, 2,2.4-)limethylhexane diisocyanate, lysine diisocyanate, 2,6-diincyanate methyl caproate, bis(2-incyanate ethyl) fumarate, bis(2-incyanate ethyl)
carbonate, 2-isocyanate ethyl-2,6-diicyanate hexanoate; isophorocyanate (IPDI), dicyclohexylmethane diisocyanate (hydrogenated MDI), cyclohexylene diisocyanate, methylcibis(2-isocyanatoethyl) 4
-Cyclohexene 1,2-dicarboxylate; xylylene diisocyanate, diethylbenzene diisocyanate; water modified product of HDI; tolylene diisocyanate (
TDI), crude TDL diphenylmethane diisocyanate (MDI), modified MDI (carposiimide modified M
DI, etc.), naphthylene diisocyanate; and mixtures of two or more of these.
本発明の組成物は、(a)中でエポキシ樹脂を硬化剤お
よび/または硬化触媒により硬化させることにより製造
することができる。The composition of the present invention can be produced by curing the epoxy resin in (a) with a curing agent and/or curing catalyst.
硬化剤は通常、エポキシ樹脂のエポキシ基と当量近辺(
同じ当量数程度)の量用いられるが、何れかを過剰に(
たとえばlO%程度またはそれ以上)存在させてもよい
。The curing agent is usually around the equivalent of the epoxy group in the epoxy resin (
(approximately the same number of equivalents), but if one is used in excess (
For example, about 10% or more) may be present.
硬化触媒は通常のエポキシ樹脂の硬化に用いられる程度
の量、通常エポキシ樹脂の0.5〜20重量%、好まし
くは0.5〜lO重量%が用いられる。The curing catalyst is used in an amount normally used for curing epoxy resins, usually 0.5 to 20% by weight, preferably 0.5 to 10% by weight of the epoxy resin.
(メタ)アクリル性不飽和結合を有する化合物(a)の
配合量は特に限定されないが(a)およびエポキシ樹脂
、硬化剤および/または硬化触媒の合計重量100部に
対して通常30〜80部、好ましくは40〜70部であ
る。The amount of compound (a) having a (meth)acrylic unsaturated bond is not particularly limited, but is usually 30 to 80 parts per 100 parts of the total weight of (a), epoxy resin, curing agent and/or curing catalyst, Preferably it is 40 to 70 parts.
反応は通常20〜170°C1好ましくは40〜150
℃で1分子中に少なくとも1個の(メタ)アクリル性不
飽和結合を有する化合物(a)中にエポキシ樹脂、硬化
剤および/または硬化触媒を混合溶解して行う。The reaction is usually carried out at 20 to 170°C, preferably 40 to 150°C.
This is carried out by mixing and dissolving an epoxy resin, a curing agent and/or a curing catalyst in a compound (a) having at least one (meth)acrylic unsaturated bond in one molecule at °C.
(a)中に分散されたエポキシ樹脂硬化物の粒子(b)
の含を率は樹脂組成物の重量に基づいて、通常20〜7
0重量%、好ましくは30〜60重量%である。エポキ
シ樹脂硬化物の粒子が20重量%未満では弾性率改善の
効果が少なく、70重量%を越えると樹脂組成物の粘度
が著しく上昇し作業性が悪くなる。Particles of cured epoxy resin dispersed in (a) (b)
The weight ratio is usually 20 to 7 based on the weight of the resin composition.
0% by weight, preferably 30-60% by weight. If the amount of particles of the cured epoxy resin is less than 20% by weight, the effect of improving the elastic modulus will be small, and if it exceeds 70% by weight, the viscosity of the resin composition will increase significantly and workability will deteriorate.
本発明の組成物は必要により(a)により希釈すること
ができる。希釈に用いる(a)は組成物を製造するのに
用いたものと同一でも異なっていてもよい。The composition of the present invention can be diluted with (a) if necessary. (a) used for dilution may be the same or different from that used to prepare the composition.
本発明の組成物を用いて成形体を製造するときには本発
明の組成物に必要によりラジカル重合開始剤(重合開始
剤と略記)およびその他の添加剤を加えラジカル重合に
より硬化物を得る。When producing a molded article using the composition of the present invention, a radical polymerization initiator (abbreviated as polymerization initiator) and other additives are added to the composition of the present invention as necessary, and a cured product is obtained by radical polymerization.
重合開始剤としては、例えば2,2°−アゾビスイソブ
チロニトリル(A I B N)、2,2゛−アゾビス
−(2,4−ジメチルバレロニトリル)(AVN)など
のアゾ化合物; ジベンゾイルパーオキンド、ジクミル
パーオキシド、ジーtertブチルパーオキサイド、t
ert−ブチルパーオキシベンゾエートN tert
−ブチルパーオキシ−2−エチルヘキサノエート、メチ
ルエチルケトンパーオキサイド、シクロヘキサノンパー
オキサイドなど過酸化物など通常のラジカル重合に用い
られる重合開始剤が使用できる。Examples of the polymerization initiator include azo compounds such as 2,2°-azobisisobutyronitrile (AIBN) and 2,2′-azobis-(2,4-dimethylvaleronitrile) (AVN); benzoyl peroxide, dicumyl peroxide, di-tert butyl peroxide, t
ert-Butyl peroxybenzoate N tert
Polymerization initiators commonly used in radical polymerization can be used, such as peroxides such as -butylperoxy-2-ethylhexanoate, methyl ethyl ketone peroxide, and cyclohexanone peroxide.
また反応速度のコントロールのために、必要により通常
の重合促進剤(ナフテン酸コバルト、ジメチルアニリン
など)、重合調節剤(ラウリルメルカプタン、α−メチ
ルスチレンダイマーなど)などが使用できる。Further, in order to control the reaction rate, ordinary polymerization accelerators (cobalt naphthenate, dimethylaniline, etc.), polymerization regulators (lauryl mercaptan, α-methylstyrene dimer, etc.), etc. can be used if necessary.
重合開始剤、重合促進剤、重合調節剤の使用量はそれぞ
れ本発明の組成物の全量に基づいて0.1〜20、好ま
しくは0.2〜lO重量%である。The amount of the polymerization initiator, polymerization accelerator, and polymerization regulator used is 0.1 to 20% by weight, preferably 0.2 to 10% by weight, based on the total amount of the composition of the present invention.
必要により使用できるその他の添加剤としては、難燃剤
(リン化合物、ハロゲン化合物、アンチモン化合物など
)、着色剤(顔料、染料)、内部離型剤、老化防止剤、
抗酸化剤、可塑剤、殺菌剤およびカーボンブランク、酸
化亜鉛、ガラスバルーン、有機バルーンおよびその他の
添加剤が挙げられる。Other additives that can be used as necessary include flame retardants (phosphorus compounds, halogen compounds, antimony compounds, etc.), colorants (pigments, dyes), internal mold release agents, anti-aging agents,
Antioxidants, plasticizers, disinfectants and carbon blanks, zinc oxide, glass balloons, organic balloons and other additives are included.
本発明の組成物を用いて成形体を製造する方法は特に限
定されない。たとえば、本発明の組成物、重合開始剤お
よびその他の添加剤の配合物を型内に常圧で、または必
要により加圧して、または型内を減圧にして注入し硬化
させる方法などがあげられる。具体例としては注型成形
、射出成形、リアクションインジェクションモールディ
ング、レジンインジェクション、圧縮成形、押出成形、
トランスファー成形などがあげられる。There are no particular limitations on the method for producing a molded article using the composition of the present invention. For example, a method of injecting the composition of the present invention, a polymerization initiator, and other additives into a mold at normal pressure, applying pressure if necessary, or under reduced pressure inside the mold and curing the mixture can be mentioned. . Specific examples include cast molding, injection molding, reaction injection molding, resin injection, compression molding, extrusion molding,
Examples include transfer molding.
C実施例コ
以下、実施例により本発明を更に説明するが、本発明は
これに限定されるものではない。EXAMPLE C The present invention will be further explained below with reference to Examples, but the present invention is not limited thereto.
以下において部は重量部を示す。In the following, parts indicate parts by weight.
実施例および比較例において使用した原料は次の通りで
ある。The raw materials used in the examples and comparative examples are as follows.
アクリル化合物(A): 1モルの分子i130(10
のポリオキシプロピレングリコール、2モルのトリクジ
イソンアネートおよび2モルのヒドロキシエチルアクリ
レートから製造したウレタンアクリレート
アクリル化合物(B)= 1モルの分子量2000のオ
キシプロピレングリコール、2モルのトリレンジイソシ
アネートおよび2モルのヒドロキシエチルアクリレート
から製造したウレタンアク1炒−ト
アクリル化合物(C): ビスフェノールAE04モル
付加物のジアクリレート
エポキシ樹脂: ビスフェノールAジグリシジルエーテ
ル(エピコート−828=油化シエルエポキシ(株)製
)
エポキシ硬化剤: ジアミノジフェニルメタン重合開始
剤: tert−ブチルパーオキシ−2−エチルヘキサ
ノエート(パーブチル0:日本油脂(株)製)
実施例1
撹拌棒、温度計、窒素導入管を備えた、スチール製反応
容器に、アクリル化合物(A)500部、エポキシ樹脂
389部、エポキシ硬化剤 111部を仕込み、窒素
気流下60℃に昇温した。Acrylic compound (A): 1 mole of molecules i130 (10
Urethane acrylate acrylic compound (B) prepared from polyoxypropylene glycol, 2 mol of tricdiisonanate and 2 mol of hydroxyethyl acrylate = 1 mol of oxypropylene glycol with a molecular weight of 2000, 2 mol of tolylene diisocyanate and 2 mol Urethane acrylate compound (C) produced from hydroxyethyl acrylate: Diacrylate epoxy resin of bisphenol AE 04 mole adduct: Bisphenol A diglycidyl ether (Epicote-828=manufactured by Yuka Ciel Epoxy Co., Ltd.) Epoxy curing Agent: Diaminodiphenylmethane polymerization initiator: tert-butylperoxy-2-ethylhexanoate (perbutyl 0: manufactured by NOF Corporation) Example 1 Steel reaction vessel equipped with a stirring bar, thermometer, and nitrogen inlet tube A container was charged with 500 parts of acrylic compound (A), 389 parts of epoxy resin, and 111 parts of epoxy curing agent, and the temperature was raised to 60° C. under a nitrogen stream.
均一に混合溶解した後、100℃に加熱し、5時間反応
してエポキシ樹脂硬化物含量50%の白色不透明クリー
ム状の樹脂組成物(1)を得た。25℃におけるこのも
のの粘度は14 r O00c pS N 比重は1
.12であった。また、40°Cで1ケ月間以上、安定
に分散したままであった。After uniformly mixing and dissolving, the mixture was heated to 100°C and reacted for 5 hours to obtain a white opaque creamy resin composition (1) containing 50% of cured epoxy resin. The viscosity of this material at 25°C is 14 r O00c pS N The specific gravity is 1
.. It was 12. Moreover, it remained stably dispersed for more than one month at 40°C.
実施例2
実施例1と同様に、アクリル化合物(B)500部、エ
ポキシ樹脂 383部、エポキシ硬化剤 111部、を
仕込み、窒素気流下60℃に昇温した。Example 2 In the same manner as in Example 1, 500 parts of the acrylic compound (B), 383 parts of the epoxy resin, and 111 parts of the epoxy curing agent were charged, and the temperature was raised to 60° C. under a nitrogen stream.
実施例1と同様に操作し、エポキシ樹脂硬化物含量50
%の白色不透明クリーム状の樹脂組成物(2)を得た。The procedure was carried out in the same manner as in Example 1, and the epoxy resin cured product content was 50.
% of a white opaque cream-like resin composition (2) was obtained.
25℃におけるこのものの粘度は、15 +000 c
pSN 比重は1.12であった。The viscosity of this at 25°C is 15 +000 c
pSN specific gravity was 1.12.
比較例1
7 りIJ ル化合物(A)500FfBに炭酸力ルノ
ウム500部を分散させ、白色クリーム状の組成物(3
)を得た。25℃におけるこのものの粘度は50,00
0CpS1 比重は1.90であった。また、40℃で
放置しておいたところ、炭酸カルシウムが1〜2日で沈
降した。Comparative Example 1 7 500 parts of carbonate compound (A) was dispersed in 500FfB to form a white creamy composition (3
) was obtained. The viscosity of this material at 25°C is 50,00
0CpS1 specific gravity was 1.90. Moreover, when it was left to stand at 40°C, calcium carbonate precipitated in 1 to 2 days.
試験例1
実施例1.2および比較例1で得られた組成物(1)〜
(3)を用いて表1の配合物を得、これを4mmの間隙
ををする2枚のガラス板で作ったモールドに注型し、7
5℃×1時間+100’Cx1時間硬化した。これらの
代表的物性を示す。Test Example 1 Compositions (1) obtained in Example 1.2 and Comparative Example 1
(3) was used to obtain the formulation shown in Table 1, which was poured into a mold made of two glass plates with a gap of 4 mm.
Curing was performed at 5°C x 1 hour + 100'C x 1 hour. Their representative physical properties are shown below.
表1
(3)HDT(熱変形温度) : JIS K−11
i911に準ず。 (単位 ℃)
(4)弾性率および強度(引張試験):JIsK−69
11に準ず。 (単位 Kg/mm2)(5)衝撃強度
(ノツチ付きIZoo) : JIS K−6911
に準ず。 (単位 Kg 、cm/cm2)[発明の効
果コ
本発明の熱硬化性樹脂組成物は高分子量の重合体がミク
ロに安定に分散された(メタ)アクリル性不飽和結合を
有する化合物(a)を基体としており、従来の無機フィ
ラー配合系に比べその欠点である分散安定性、配合物の
比重、配合物の粘度を改善している。従って、本発明の
熱硬化性樹脂組成物は、例えば注型、ボッティング、エ
ンキャプシュレーション、反応射出成形用材料や積層品
、接着剤、塗料等の各種用途において有用であり、(注
)(1)粘度二 B型粘度計を用い、25℃で測定。Table 1 (3) HDT (heat distortion temperature): JIS K-11
According to i911. (Unit: °C) (4) Elastic modulus and strength (tensile test): JIsK-69
According to 11. (Unit: Kg/mm2) (5) Impact strength (notched IZoo): JIS K-6911
According to. (Unit: Kg, cm/cm2) [Effects of the Invention The thermosetting resin composition of the present invention is a compound (a) having (meth)acrylic unsaturated bonds in which a high molecular weight polymer is stably dispersed microscopically. It improves dispersion stability, specific gravity of the blend, and viscosity of the blend compared to conventional inorganic filler blend systems. Therefore, the thermosetting resin composition of the present invention is useful in various applications such as casting, botting, encapsulation, reaction injection molding materials, laminates, adhesives, paints, etc. (Note) (1) Viscosity 2 Measured at 25°C using a B-type viscometer.
(単位 cps)
(2)硬度(ShoreD): ASTM D−22
40ヒーー−」(Unit: cps) (2) Hardness (ShoreD): ASTM D-22
40 hee-”
Claims (1)
飽和結合を有する化合物(a)中に分散されたエポキシ
樹脂硬化物の粒子(b)を含むことを特徴とする熱硬化
性樹脂組成物。 2、(b)が(a)中でエポキシ樹脂を硬化反応させて
なるエポキシ樹脂硬化物の粒子である請求項1記載の組
成物。[Claims] 1. It is characterized by containing particles (b) of a cured epoxy resin dispersed in a compound (a) having at least one (meth)acrylic unsaturated bond in each molecule. A thermosetting resin composition. 2. The composition according to claim 1, wherein (b) is particles of a cured epoxy resin obtained by subjecting an epoxy resin to a curing reaction in (a).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20081790A JPH0485323A (en) | 1990-07-27 | 1990-07-27 | Thermosetting resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20081790A JPH0485323A (en) | 1990-07-27 | 1990-07-27 | Thermosetting resin composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0485323A true JPH0485323A (en) | 1992-03-18 |
Family
ID=16430694
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP20081790A Pending JPH0485323A (en) | 1990-07-27 | 1990-07-27 | Thermosetting resin composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0485323A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006265483A (en) * | 2005-03-25 | 2006-10-05 | Kaneka Corp | Curable composition for both thermal radical curing/thermal cation curing |
-
1990
- 1990-07-27 JP JP20081790A patent/JPH0485323A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006265483A (en) * | 2005-03-25 | 2006-10-05 | Kaneka Corp | Curable composition for both thermal radical curing/thermal cation curing |
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