TWI573812B - Thermosetting composition - Google Patents
Thermosetting composition Download PDFInfo
- Publication number
- TWI573812B TWI573812B TW100113898A TW100113898A TWI573812B TW I573812 B TWI573812 B TW I573812B TW 100113898 A TW100113898 A TW 100113898A TW 100113898 A TW100113898 A TW 100113898A TW I573812 B TWI573812 B TW I573812B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin
- compound
- group
- resin composition
- carbon atoms
- Prior art date
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- 239000000203 mixture Substances 0.000 title description 5
- 229920001187 thermosetting polymer Polymers 0.000 title description 4
- 229920005989 resin Polymers 0.000 claims description 69
- 239000011347 resin Substances 0.000 claims description 69
- -1 imidazole compound Chemical class 0.000 claims description 67
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 42
- 239000011342 resin composition Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000004593 Epoxy Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000011888 foil Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000004035 construction material Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 150000001913 cyanates Chemical class 0.000 description 14
- 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 12
- 239000000835 fiber Substances 0.000 description 12
- 229920003986 novolac Polymers 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
- 239000011889 copper foil Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 8
- 238000001879 gelation Methods 0.000 description 8
- 239000003365 glass fiber Substances 0.000 description 8
- RNIPJYFZGXJSDD-UHFFFAOYSA-N 2,4,5-triphenyl-1h-imidazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 RNIPJYFZGXJSDD-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 229910000420 cerium oxide Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 5
- 238000004321 preservation Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- 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 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 239000004643 cyanate ester Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical group C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- 239000011490 mineral wool Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 3
- JRQJLSWAMYZFGP-UHFFFAOYSA-N 1,1'-biphenyl;phenol Chemical compound OC1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 JRQJLSWAMYZFGP-UHFFFAOYSA-N 0.000 description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910001593 boehmite Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000000816 ethylene group Polymers [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
- 239000012784 inorganic fiber Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 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 2
- 238000010030 laminating Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000005078 molybdenum compound Substances 0.000 description 2
- 150000002752 molybdenum compounds Chemical class 0.000 description 2
- ZCIJAGHWGVCOHJ-UHFFFAOYSA-N naphthalene phenol Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)O ZCIJAGHWGVCOHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920002577 polybenzoxazole Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 239000007787 solid Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- NHWYMYDMYCNUKI-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3,5-diethylphenyl]methyl]-2,6-diethylphenyl]pyrrole-2,5-dione Chemical compound C=1C(CC)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(CC)=C1N1C(=O)C=CC1=O NHWYMYDMYCNUKI-UHFFFAOYSA-N 0.000 description 1
- RUORVEVRVBXRIO-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3,5-dimethylphenyl]methyl]-2,6-dimethylphenyl]pyrrole-2,5-dione Chemical compound C=1C(C)=C(N2C(C=CC2=O)=O)C(C)=CC=1CC(C=C1C)=CC(C)=C1N1C(=O)C=CC1=O RUORVEVRVBXRIO-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-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 class 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
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 description 1
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- XWULMVRLWXONCN-UHFFFAOYSA-N 4-[2-(4-cyanophenyl)propan-2-yl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(C)(C)C1=CC=C(C#N)C=C1 XWULMVRLWXONCN-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004812 Fluorinated ethylene propylene Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
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- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- KEGIEOGUARJXQU-UHFFFAOYSA-L manganese(2+);naphthalene-1-carboxylate Chemical compound [Mn+2].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 KEGIEOGUARJXQU-UHFFFAOYSA-L 0.000 description 1
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
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- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910003468 tantalcarbide Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/681—Metal alcoholates, phenolates or carboxylates
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- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Landscapes
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Description
本發明係關於一種樹脂組成物,更詳而言之,係關於一種形成電氣回路之印刷電路板材料等所使用之樹脂組成物,使該樹脂組成物含浸或塗佈於基材之預漬物、及使其預漬物硬化所得到之層合板。
含有使含有氰酸酯化合物的氰酸酯樹脂、或氰酸酯化合物與雙馬來醯亞胺化合物反應之化合物的雙馬來醯亞胺三嗪樹脂(BT樹脂)係自古已為人所知作為高耐熱性或介電特性等優異之熱硬化性樹脂。近年,此等之樹脂係被廣泛使用於半導體塑膠封裝體用等之高功能印刷電路板用材料等(例如專利文獻1、2)。
在上述氰酸酯樹脂或BT樹脂中係為提高硬化速度而提昇生產性,故進行使各種之觸媒添加於樹脂。如此之觸媒已提出咪唑化合物(專利文獻3、4及5)。藉由於樹脂中添加咪唑化合物,可顯現觸媒活性,預漬物製造時,在含浸塗佈後之乾燥步驟中,可使樹脂以低溫且短時間硬化,又,亦可以低溫且短時間進行預漬物之層合沖壓成形。
但,若於樹脂中添加咪唑化合物,預漬物或層合板之生產性可提高,但預漬物之保存安定性會降低等問題仍存在。
專利文獻1:特開2007-204697號公報
專利文獻2:特開2008-88400號公報
專利文獻3:特開2005-281513號公報
專利文獻4:特許3821797號公報
專利文獻5:特許3821728號公報
本發明人等係得到如下見識:藉由於氰酸酯樹脂或BT樹脂中添加環氧樹脂與特定之咪唑化合物,俾可實現一種可以低溫且短時間進行預漬物之含浸塗佈後的乾燥步驟或層合沖壓成形,同時亦可維持預漬物的保存安定性之樹脂組成物。本發明係以如此之見識所得到者。
因此,本發明之目的係在於提供一種樹脂組成物,其係可以低溫且短時間進行預漬物之含浸塗佈後的乾燥步驟或層合沖壓成形,同時亦可維持預漬物的保存安定性之樹脂組成物。
繼而,本發明之樹脂組成物,其係含有以下述式(I)所示之咪唑化合物(A)、環氧化合物(B)、氰酸酯化合物(C1)或BT樹脂(C2)而成;
(式中,R1及R2分別獨立表示碳數3~18的烷基、碳數3~18的烯基、碳數3~18的烷氧基、或碳數6~14之取代或非取代之芳香族取代基,R3係表示氫、碳數1~18的烷基、碳數2~18的烯基、碳數1~18的烷氧基、或碳數6~14之取代或非取代之芳香族取代基或鹵素基)。
若依本發明,係可實現一種可以低溫且短時間進行預漬物之含浸塗佈後的乾燥步驟或層合沖壓成形,同時亦可維持預漬物的保存安定性之樹脂組成物。因此,可使優異之耐熱性及吸濕耐熱性的含氰酸酯化合物的樹脂或BT樹脂之生產性與保存安定性併存。
本發明之樹脂組成物係含有特定之咪唑化合物(A)、環氧化合物(B)、氰酸酯化合物(C1)或BT樹脂(C2)作為必要成份。以下,說明有關構成本發明之樹脂組成物的各成分。
本發明之樹脂組成物,係含有以下述式(I)所示之咪唑化合物(A)。
在上述式(I)中,R1及R2分別獨立表示碳數3~18的烷基、碳數3~18的烯基、碳數3~18的烷氧基、或碳數6~14之取代或非取代之芳香族取代基。芳香族取代基之氫原子的至少一個被其他取代基取代時,如此之取代基可舉例如碳數1~18的烷基、碳數2~18的烯基、碳數1~18的烷氧基及鹵素基。
從聚合反應之硬化促進及預漬物之保存安定性的觀點,宜R1及R2分別獨立表示異丙基、第三丁基、異丙基烷氧基、第三丁基烷氧基、苯基、或萘基,尤宜R1及R2任一者均為苯基。
在上述式(I)中,R3表示氫、碳數1~18的烷基、碳數2~18的烯基、碳數1~18的烷氧基、或碳數6~14之取代或非取代之芳香族取代基或鹵素基。芳香族取代基之氫原子的至少一個被其他取代基取代時,如此之取代基可舉例如碳數1~18的烷基、碳數2~18的烯基、碳數1~18的烷氧基及鹵素基。
在本發明中係在含有氰酸酯化合物(C1)或BT樹脂(C2)之樹脂組成物中,藉由添加如上述之特定的咪唑化合物(A)作為硬化觸媒,可使優異之耐熱性及吸濕耐熱性的含氰酸酯化合物的樹脂或BT樹脂之生產性與保存安定性併存。此理由係不確定,但如以下般想法。亦即,認為於咪唑化合物中之反應活性點的2級胺附近具有龐大的取代基之特定咪唑化合物(A)係在高溫時分子運動能量高,顯現2級胺之觸媒活性,但在低溫時分子運動能量低,可抑制2級胺之觸媒活性,故使生產性(硬化速度)與保存安定性併存。
上述咪唑化合物(A)係從硬化促進效果、保存安定性及成形性之觀點,相對於樹脂之總量宜含有0.1~10質量份,更宜為0.2~5質量份。又,只要無特別聲明,所謂樹脂之總量係咪唑化合物(A)、環氧化合物(B)、氰酸酯化合物(C1)或BT樹脂(C2)之合計質量者。
本發明之樹脂組成物係除了上述咪唑化合物(A)外,尚亦可含有其他公知之硬化促進劑。如此之硬化促進劑可舉例如過氧化苯甲醯基、月桂醯基過氧化物、乙醯基過氧化物、對氯苯甲醯基過氧化物、二第三丁基-二過酞酸酯等所例示之有機過氧化物、偶氮雙腈之偶氮化合物、N,N-二甲基苯甲基胺、N,N-二甲基苯胺、N,N-二甲基甲苯胺、2-N-乙基苯胺基乙醇、三正丁基胺、吡啶、喹啉、N-甲基嗎啉、三乙醇胺、三亞乙基二胺、四甲基丁烷二胺、N-甲基六氫吡啶等之第3級胺類、酚、二甲酚、甲酚、間苯二酚、兒茶酚等之酚類、萘烷酸鉛、硬脂酸鉛、萘烷酸鋅、辛酸鋅、油酸錫、二丁基錫馬來酸酯、萘烷酸錳、萘烷酸鈷、乙醯基丙酮鐵等之有機金屬鹽、此等有機金屬鹽溶解於酚、雙酚等之含羥基的化合物者、氯化錫、氯化鋅、氯化鋁等之無機金屬鹽、二辛基錫氧化物、其他之烷基錫、烷基錫氧化物等之有機錫化合物等。
在本發明所使用之環氧化合物(B)係只要為於1分子中具有2個以上之環氧基的化合物即可,無特別限制,可使用公知者。在本發明中,較佳之環氧化合物(B)係可舉例如將於1分子中具有2個以上之羥基的化合物之羥基的氫原子取代成縮水甘油基之構造者。又,環氧化合物(B)宜為具有芳香族基者,可適宜使用縮水甘油基直接鍵結於芳香族基之構造者。如此之環氧化合物,可舉例如使雙酚A、雙酚F、雙酚M、雙酚P、雙酚E、酚酚醛清漆樹脂、甲酚酚醛清漆樹脂、二環戊二烯酚醛清漆樹脂、四甲基雙酚F、雙酚A酚醛清漆樹脂、溴化雙酚A、溴化酚酚醛清漆樹脂、3官能酚、4官能酚、萘型酚、聯苯基型酚、酚芳烷基樹脂、聯苯基芳烷基樹脂、萘酚芳烷基樹脂、二環戊二烯芳烷基樹脂、脂環式酚、含有磷之酚等的羥基之氫原子取代成縮水甘油基之構造的化合物、或、縮水甘油基胺、縮水甘油基酯、丁二烯等之雙鍵環氧基化的化合物、含有羥基之聚矽氧樹脂類與表氯醇等之反應所得到的化合物等。此等之環氧化合物(B)係可單獨或適當組合2種以上而使用。又,上述之環氧化合物(B)係可為單體、寡聚物及樹脂之任一者的形態。
環氧化合物(B)從吸濕耐熱性及耐熱性之觀點,相對於樹脂之總量宜含有25~95質量%,更宜為30~90質量%。
在本發明所使用之氰酸酯化合物(C1)係只要為於1分子中具有2個以上之氰酸酯基的化合物即可,無特別限制,可使用公知者。在本發明中,較佳之氰酸酯化合物(C1)係可舉例如將於1分子中具有2個以上之羥基的化合物之羥基取代成氰酸酯基之構造者。又,氰酸酯化合物(C1)宜為具有芳香族基者,可適宜使用氰酸酯基直接鍵結於芳香族基之構造者。如此之氰酸酯化合物,可舉例如使雙酚A、雙酚F、雙酚M、雙酚P、雙酚E、酚酚醛清漆樹脂、甲酚酚醛清漆樹脂、二環戊二烯酚醛清漆樹脂、四甲基雙酚F、雙酚A酚醛清漆樹脂、溴化雙酚A、溴化酚酚醛清漆樹脂、3官能酚、4官能酚、萘型酚、聯苯基型酚、酚芳烷基樹脂、聯苯基芳烷基樹脂、萘酚芳烷基樹脂、二環戊二烯芳烷基樹脂、脂環式酚、含有磷之酚等的羥基取代成氰酸酯基之構造者。此等之氰酸酯化合物(C1)係可單獨或適當組合2種以上而使用。又,上述之氰酸酯化合物(C1)係可為單體、寡聚物及樹脂之任一者的形態。
上述氰酸酯化合物(C1)係可依以往公知之方法進行製造,例如,可藉由於1分子中具有2個以上之羥基的化合物與鹵化氰等之反應來得到。
氰酸酯化合物(C1)從吸濕耐熱性及耐熱性之觀點,相對於樹脂之總量宜含有5~75質量%,更宜為10~70質量%。
在本發明所使用之BT樹脂(C2)係使上述之氰酸酯化合物(C1)與馬來醯亞胺化合物以無溶劑進行加熱溶融混合,或,溶解於適當的有機溶劑而加熱混合,進行聚合物化者。為使氰酸酯化合物(C1)與馬來醯亞胺化合物混合所使用之有機溶劑可舉例如甲乙酮、N-甲基吡咯烷酮、二甲基甲醯胺、二甲基乙醯胺、甲苯、二甲苯等。
製造BT樹脂(C2)時所使用之馬來醯亞胺化合物係只要為於1分子中具有1個以上之馬來醯亞胺基的化合物即可,無特別限定。可舉例如N-苯基馬來醯亞胺、N-氫苯基馬來醯亞胺、雙(4-馬來醯亞胺苯基)甲烷、2,2-雙[4-(4-馬來醯亞胺苯氧基)-苯基]丙烷、雙(3,5-二甲基-4-馬來醯亞胺苯基)甲烷、雙(3-乙基-5-甲基-4-馬來醯亞胺苯基)甲烷、雙(3,5-二乙基-4-馬來醯亞胺苯基)甲烷等。此等之馬來醯亞胺係可單獨或適當組合2種以上而使用。
BT樹脂(C2)從吸濕耐熱性及耐熱性之觀點,相對於樹脂之總量宜含有5~75質量%,更宜為10~70質量%。
本發明之樹脂組成物係亦可進一步含有馬來醯亞胺化合物(D)。馬來醯亞胺化合物(D)可適宜使用上述者。馬來醯亞胺化合物(D)之含量係從吸濕耐熱性之觀點,相對於樹脂之總量宜為50質量%以下,更宜為40質量%以下。又,此處之所謂樹脂的總量係咪唑化合物(A)、環氧化合物(B)、氰酸酯化合物(C1)或BT樹脂(C2)與馬來醯亞胺化合物(D)之合計質量者。
又,樹脂組成物係亦可含有無機填充材。藉由添加無機填充材,可對樹脂賦予低熱膨脹化、耐燃性及雷射加工性,同時並可控制預漬物或層合體之成形時的樹脂之流動性。在本發明所使用之無機系填充材,無特別限制而可使用公知者,可舉例如天然二氧化矽、熔融二氧化矽、非晶形二氧化矽、發煙二氧化矽、中空二氧化矽等之二氧化矽類、氫氧化鋁、氫氧化鋁加熱處理品(加熱處理氫氧化鋁,減少結晶水之一部分者)、水軟鋁石、氫氧化鎂等之金屬氫氧化物、氧化鉬、鉬酸鋅等之鉬化合物、氧化鈦、鈦酸鋇、硫酸鋇、硼酸鋅、錫酸鋅、氧化鋁、泥土、高嶺土、滑石、燒成泥土、燒成高嶺土、燒成滑石、雲母、玻璃短纖維(E玻璃或D玻璃等之玻璃微粉末類)、中空玻璃等。此等之中,從耐燃性之觀點,可適宜使用氫氧化鋁、氫氧化鋁加熱處理品(加熱處理氫氧化鋁,減少結晶水之一部分者)、水軟鋁石、氫氧化鎂等之金屬水合物、氧化鉬、鉬酸鋅等之鉬化合物。此等之無機填充材係可單獨或適當組合2種以上而使用。
無機填充材係從線膨脹率、耐燃性及成形性之觀點,,相對於樹脂總量宜含有10~600質量%,更宜為30~500質量%。
本發明之樹脂組成物係上述成分以外,亦可依需要而含有其他之成分。在無損所希望的特性之範圍中,亦可添加其他之熱硬化性樹脂、熱塑性樹脂、及其寡聚物或彈性體類等之各種的高分子化合物、其他之耐燃性的化合物、添加劑等。此等係只要為一般所使用者即可,並無特別限制。可舉例如磷酸酯、磷酸三聚氰胺等之磷化合物、三聚氰胺或苯並胍胺等之含氮的化合物、含有噁嗪環的化合物、矽系化合物、聚醯亞胺、聚乙烯基乙縮醛、苯氧樹脂、丙烯酸樹脂、具有羥基或羧基之丙烯酸樹脂、醇酸樹脂、熱塑性聚胺基甲酸酯樹脂、聚丁二烯、丁二烯-丙烯腈共聚物、聚氯丁烯、丁二烯-苯乙烯共聚物、聚異戊二烯、丁基橡膠、氟橡膠、天然橡膠等之彈性體類、苯乙烯-異戊二烯橡膠、丙烯酸橡膠、此等之核殼橡膠、環氧基化丁二烯、馬來酸化丁二烯、聚乙烯、聚丙烯、聚乙烯-丙烯共聚物、聚-4-甲基戊烯-1、聚氯化乙烯、聚偏氯乙烯、聚苯乙烯、聚乙烯基甲苯、聚乙烯基酚、AS樹脂、ABS樹脂、MBS樹脂、聚-4-氟化乙烯、氟化乙烯-丙烯共聚物、4-氟化乙烯-6-氟化乙烯共聚物、偏氟乙烯等之乙烯基化合物聚合物類、聚碳酸酯、聚酯碳酸酯、聚苯醚、聚碸、聚酯、聚醚碸、聚醯胺、聚醯胺醯亞胺、聚酯醯亞胺、聚苯硫謎等之熱塑性樹脂類及此等之低分子量聚合物類、(甲基)丙烯酸酯、環氧基(甲基)丙烯酸酯、二(甲基)丙烯醯氧-雙酚等之聚(甲基)丙烯酸酯類、苯乙烯、乙烯基吡咯烷酮、二丙烯酸基酞酸酯、二乙烯基苯、二烯丙基苯、二烯丙基醚雙酚、三烯基三聚異氰酸酯等之聚烯丙基化合物及其預聚物類、二環戊二烯及其預聚物類、酚樹脂、不飽和聚酯等之含聚合性雙鍵的單體類及其預聚物類、聚異氰酸酯等之熱硬化性單體或其預聚物類等。添加劑可舉例如紫外線吸收劑、抗氧化劑、光聚合起始劑、螢光增白劑、光增感劑、染料、顏料、增黏劑、滑劑、消泡劑、分散劑、流平劑、光澤劑、聚合抑制劑等,此等添加劑係亦可依需要而單獨或適當組合2種以上而使用。
本發明之樹脂組成物係藉加熱進行硬化。硬化條件係依樹脂組成物之組成或硬化促進劑的咪唑化合物(A)之調配量等而變化。使樹脂組成物完全硬化時,一般在100~300℃的範圍,進行特定時間的加熱。亦可在加壓環境下加熱,例如在0.1~5MPa、宜為0.5~3MPa的加壓下,使樹脂組成物硬化。
如上述做法所得到之硬化物係可從其優異之物性或作業性利用於各種之用途。本發明之樹脂組成物的適宜用途可舉例如預漬物、銅箔層合板等的印刷電路板用材料、構造材料、澆鑄用樹脂等。
預漬物係使上述之樹脂組成物含浸或塗佈於基材者。基材係可使用於各種印刷電路板材料所使用之公知無機或有機之纖維補強材。無機纖維質補強材可舉例如E、NE、D、S、T玻璃等之玻璃纖維、石英玻璃纖維、碳纖維、氧化鋁纖維、碳化矽纖維、石綿、岩綿、渣綿、石膏晶鬚等之無機纖維、或其織布或不織布、或此等之混合物。又,有機纖維質補強材可舉例如全芳香族聚醯胺纖維、聚醯亞胺纖維、液晶聚酯、聚酯纖維、氟纖維、聚苯並噁唑纖維、綿、麻、半碳纖維等之有機纖維或其織布或不織布、或此等之混合物。
上述無機或有機之纖維質補強材依需要而亦可單獨或適宜組合2種以上而使用。例如玻璃纖維與全芳香族聚醯胺纖維、玻璃纖維與碳纖維、玻璃纖維與聚醯胺纖維、玻璃纖維與液晶性芳香族聚酯等混纖布、玻璃紙、雲母紙、氧化鋁紙等之無機質紙、牛皮紙、綿紙、紙-玻璃混抄紙等之組合、或組合此等2種類以上。
上述之基材係為提昇與樹脂之密著性,亦可實施表面處理。表面處理係可使用在預漬物或層合板所適用的以往公知的方法。又,使用於薄物用途之基材係可適宜使用於聚醯亞胺薄膜、全芳香族聚醯胺薄膜、聚苯並噁唑薄膜、液晶聚酯薄膜等。
預漬物係可藉由使上述之樹脂組成物含浸或塗佈於基材來製造。例如,使上述之樹脂組成物與有機溶劑所構成的樹脂清漆含浸或塗佈於基材後,在100~200℃之乾燥機中,加熱1~60分鐘而使樹脂半硬化來製造。樹脂組成物對基材(含有無機填充材)之含量係相對於預漬物全體宜為20~90質量%的範圍。
可藉層合上述之預漬物,成形(硬化)俾形成層合板。層合板係使上述之預漬物重疊1片或2片以上,依所希望於其單面或雙面,配置銅或鋁等之金屬箔而層合,成形(硬化)來製造。使用之金屬箔係若為可使用於印刷配線板材料者即可使用,並無特別限制。又,於層合成形係可採用一般之印刷配線板用層合板及多層板之方法。層合成形之條件係可舉例如使用多段沖壓、多段真空沖壓、連續成形、高壓鍋成形機或真空積層機等,溫度一般為100~300℃,壓力為2~100kg f/cm2、加熱時間為0.05~5小時的範圍。又,在本發明中係亦可藉由組合上述之預漬物、與另外準備之內層用的配線板而層合成形以形成多層板。
以下表示實施例及比較例,詳細說明本發明,但本發明係不限定於此等。
混合2,2-雙(4-氰酸基苯基)丙烷(CA 200、三菱瓦斯化學(股)製)25質量份、及雙(3-乙基-5-甲基-4-馬來醯亞胺苯基)甲烷(BMI-70、KI化成製)25質量份,以150℃熔融而攪拌,同時並反應6小時後,再溶解於甲乙酮以得到BT樹脂。
混合所得到之BT樹脂50質量份(固形分換算的份數)、酚酚醛清漆型環氧基(N 770、DIC製)25質量份、聯苯基芳烷基型環氧基(NC-3000-FH、日本化藥(股)製)25質量份、辛酸鋅0.02質量份、及2,4,5-三苯基咪唑(東京化成工業製)1質量份,調製清漆。使所得到之清漆含浸於厚0.1mm的E玻璃布(E10T、Unitika Glass Fiber製),以165℃乾燥至凝膠化時間成為90秒,製作樹脂量為50質量%之預漬物。重疊所得到之預漬物2片,於其上下配置厚12μm之電解銅箔(JTC-LP箔、日礦金屬製),以壓力3MPa,下述之3種類的加熱條件進行層合成形,得到絕緣層厚0.2mm之各銅箔層合板。
加熱條件1:以製品溫度220℃保持20分鐘
加熱條件2:以製品溫度200℃保持60分鐘
加熱條件3:以製品溫度200℃保持60分鐘
使2,2-雙(4-氰酸基苯基)丙烷(CA 200、三菱瓦斯化學(股)製)60質量份以150℃熔融而攪拌,同時並反應6小時後,再溶解於甲乙酮以得到預聚物。
混合所得到之預聚體60質量份(固形分換算的份數)、甲酚酚醛清漆型環氧基(N 680、DIC製)40質量份、辛酸鋅0.02質量份、及2,4,5-三苯基咪唑(東京化成工業製)1質量份,調製清漆。使所得到之清漆含浸於厚0.1mm的E玻璃布(E10T、Unitika Glass Fiber製),以170℃乾燥8分鐘,製作樹脂量為50質量%之預漬物。重疊所得到之預漬物2片,於其上下配置厚12μm之電解銅箔(JTC-LP箔、日礦金屬製),以與實施例1同樣之條件進行層合成形,得到絕緣層厚0.2mm之銅箔層合板。
除在實施例1中使用2-苯基、4-甲基咪唑(東京化成工業製)取代2,4,5-三苯基咪唑以外,其餘係與實施例1同樣做法,得到絕緣層厚0.2mm之銅箔層合板。
除在實施例1中不使用2,4,5-三苯基咪唑以外,其餘係與實施例1同樣做法,得到絕緣層厚0.2mm之銅箔層合板。
除在實施例2中使用2-苯基、4-甲基咪唑(東京化成工業製)取代2,4,5-三苯基咪唑以外,其餘係與實施例2同樣做法,得到絕緣層厚0.2mm之銅箔層合板。
除在實施例2中不使用2,4,5-三苯基咪唑以外,其餘係與實施例2同樣做法,得到絕緣層厚0.2mm之銅箔層合板。
對於如上述般做法所得到之各預漬物及層合板,如下述般做法而進行預漬物凝膠化時間測定、玻璃轉移溫度測定、及吸濕耐熱性評估。
使預漬物在40℃之恆溫環境下放置0、5、10、15及30日,測定各凝膠化時間。凝膠化時間之測定係依據JIS C6521(多層印刷電路板用預漬物試驗法)的硬化時間測定而進行(參照JIS C6521之5.7)。
製作大小10mm×60mm之試樣,使用DMA裝置(TA Instrument 2980型),在昇溫10℃/分之條件下進行玻璃轉移溫度之測定。測定係依據JIS C6481(印刷電路板用銅箔層合板試驗方法)的DMA法B法而進行(參照JIS C6481之5.17.2)。
從表1明顯可知,使用含有以上述式(I)所示之咪唑化合物以外的咪唑化合物之2-苯基、4-甲基咪唑之樹脂組成物的層合板(比較例1及3)中係預漬物之硬化時間短,但預漬物凝膠化時間的隨時間變化大。又,使用不含有效果促進劑之咪唑化合物的樹脂組成物之層合板(比較例2及4)中,預漬物凝膠化時間的隨時間變化少,但,預漬物之硬化時間長。然而,使用含有以上述式(I)所示之咪唑化合物的2,4,5-三苯基咪唑之樹脂組成物的層合板(實施例1及2)中係預漬物之硬化時間短,且預漬物凝膠化時間的隨時間變化少。
Claims (10)
- 一種樹脂組成物,其係含有以下述式(I)所示之咪唑化合物(A)、與環氧化合物(B)、與氰酸酯化合物(C1)或作為含有使氰酸酯化合物與雙馬來醯亞胺化合物反應所得化合物的雙馬來醯亞胺三嗪樹脂之BT樹脂(C2)而成,且前述氰酸酯化合物(C1)或前述BT樹脂(C2)係相對於樹脂之總量含有10~70質量%;
- 如申請專利範圍第1項之樹脂組成物,其中前述式(I)之R1及R2分別獨立表示異丙基、第三丁基、異丙基烷氧基、第三丁基烷氧基、苯基、或萘基。
- 如申請專利範圍第2項之樹脂組成物,其中前述式(I)之R1及R2任一者均為苯基。
- 如申請專利範圍第1~3項中任一項之樹脂組成物,其中前述咪唑化合物(A)係相對於樹脂之總量含有0.1~10 質量%而成。
- 如申請專利範圍第1~3項中任一項之樹脂組成物,其中前述環氧化合物(B)係相對於樹脂之總量含有25~95質量%而成。
- 一種預漬物,其係使如申請專利範圍第1~3項中任一項之樹脂組成物含浸或塗佈於基材。
- 一種層合板,其係使如申請專利範圍第6項之預漬物進行層合成形。
- 一種貼金屬箔之層合板,其係使如申請專利範圍第6項之預漬物與金屬箔進行層合成形。
- 一種構造材料,其係使用如申請專利範圍第1~3項中任一項之樹脂組成物。
- 一種澆鑄用樹脂,其係含有如申請專利範圍第1~3項中任一項之樹脂組成物而成。
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- 2011-04-19 JP JP2012511667A patent/JP6085172B2/ja active Active
- 2011-04-19 EP EP11772009.4A patent/EP2562196B1/en active Active
- 2011-04-19 WO PCT/JP2011/059627 patent/WO2011132674A1/ja active Application Filing
- 2011-04-19 SG SG10201503091TA patent/SG10201503091TA/en unknown
- 2011-04-19 US US13/641,985 patent/US20130101863A1/en not_active Abandoned
- 2011-04-19 KR KR1020127026948A patent/KR101840486B1/ko active IP Right Grant
- 2011-04-19 SG SG2012078093A patent/SG184967A1/en unknown
- 2011-04-21 TW TW100113898A patent/TWI573812B/zh active
-
2013
- 2013-08-05 HK HK13109097.8A patent/HK1181796A1/zh unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1237186A (zh) * | 1997-07-24 | 1999-12-01 | 洛克泰特公司 | 用作充填密封材料的热固性树脂组合物 |
Also Published As
Publication number | Publication date |
---|---|
TW201204760A (en) | 2012-02-01 |
JP6085172B2 (ja) | 2017-02-22 |
SG10201503091TA (en) | 2015-06-29 |
KR20130079339A (ko) | 2013-07-10 |
US20130101863A1 (en) | 2013-04-25 |
WO2011132674A1 (ja) | 2011-10-27 |
CN102939316A (zh) | 2013-02-20 |
KR101840486B1 (ko) | 2018-03-20 |
JPWO2011132674A1 (ja) | 2013-07-18 |
CN102939316B (zh) | 2016-04-27 |
HK1181796A1 (zh) | 2013-11-15 |
EP2562196B1 (en) | 2018-02-21 |
EP2562196A4 (en) | 2016-09-28 |
EP2562196A1 (en) | 2013-02-27 |
SG184967A1 (en) | 2012-11-29 |
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