JP6137607B2 - フェノール性水酸基含有樹脂、フェノール性水酸基含有樹脂の製造方法、硬化性樹脂組成物、その硬化物、及び放熱樹脂材料 - Google Patents
フェノール性水酸基含有樹脂、フェノール性水酸基含有樹脂の製造方法、硬化性樹脂組成物、その硬化物、及び放熱樹脂材料 Download PDFInfo
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- JP6137607B2 JP6137607B2 JP2013062047A JP2013062047A JP6137607B2 JP 6137607 B2 JP6137607 B2 JP 6137607B2 JP 2013062047 A JP2013062047 A JP 2013062047A JP 2013062047 A JP2013062047 A JP 2013062047A JP 6137607 B2 JP6137607 B2 JP 6137607B2
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- 150000003839 salts Chemical class 0.000 description 8
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- 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 5
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- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001639 boron compounds Chemical class 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WLPKFQRBARNCNR-UHFFFAOYSA-N ethene 1,3,5-triazine-2,4,6-triamine Chemical compound C=C.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 WLPKFQRBARNCNR-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-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
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 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
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
Images
Landscapes
- Reinforced Plastic Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Cooling Or The Like Of Semiconductors Or Solid State Devices (AREA)
Description
で表わされる分子構造を有するフェノール性水酸基含有樹脂は、配向性が高いことから硬化物における熱伝導性が高く、更に基材密着性や柔軟性、耐熱性にも優れることを見出し、本発明を完成するに至った。
で表わされる分子構造を有することを特徴とするフェノール性水酸基含有樹脂に関する。
又は下記一般式(2)
で表わされるジオール化合物(a)とを反応させることを特徴とするフェノール性水酸基含有樹脂の製造方法に関する。
で表わされる分子構造を有することを特徴とする。
で表される構造部位(i)、または下記一般式(ii)
[一般式(I)中のmの平均値の求め方]
下記条件でのGPC測定により得られるm=1、2、3、4、5それぞれの場合に対応するスチレン換算分子量(αm)の値と、m=1、2、3、4、5それぞれの場合に対応する理論分子量(βm)との比率(βm/αm)をそれぞれ求め、これら(βm/αm)の平均値を求める。GPC測定の結果得られる数平均分子量(Mn)に、この平均値を掛け合わせた値を平均分子量とし、この平均分子量に相当するmの値を算出する。
測定装置 :東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G4000HXL」
検出器: RI(示差屈折径)
データ処理:東ソー株式会社製「GPC−8020モデルIIバージョン4.10」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC−8020モデルIIバージョン4.10」の測定マニュアル
に準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィ
ルターでろ過したもの(50μl)。
で表される芳香核含有ジオール化合物を含有していても良く、この場合、該ジオール化合物の含有量は中5〜30質量%の範囲であることが好ましい。
又は下記一般式(2)
測定装置 :東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G4000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPC−8020モデルIIバージョン4.10」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC−8020モデルIIバージョン4.10」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)。
装置:日本電子(株)製 AL−400
測定モード:SGNNE(NOE消去の1H完全デカップリング法)
溶媒 :ジメチルスルホキシド
パルス角度:45℃パルス
試料濃度 :30wt%
積算回数 :10000回
温度計、撹拌機を取り付けたフラスコに1,6−ヘキサンジオールのジグリシジルエーテル(DIC株式会社製「EPICLON 726D」エポキシ当量124g/当量)744g(6当量)と4,4‘−ジヒドロキシジフェニルエーテル(水酸基当量101g/当量)1212g(12当量)を仕込み、140℃まで30分間要して昇温した後、4%水酸化ナトリウム水溶液5gを仕込んだ。その後、30分かけて150℃まで昇温し、150℃で3時間反応させた。反応後に中和量のリン酸ソーダを添加して、フェノール性水酸基含有樹脂(1)1900gを得た。得られたフェノール性水酸基含有樹脂(1)のGPCチャートを図1に示す。得られたフェノール性水酸基含有樹脂(1)をMSにより分析したところ、下記一般式(I−1)
[フェノール樹脂(1’)の製造]
実施例1の4,4‘−ジヒドロキシジフェニルエーテル(水酸基当量101g/当量)1212g(12当量)を、ビスフェノールA(水酸基当量114g/当量)1368g(12当量)に変更した以外は実施例1記載と同様の方法でフェノール樹脂(1’)を2000g得た。このフェノール樹脂(1’)のGPCチャートから算出される水酸基当量は262g/当量、水酸基当量から算出される前記一般式(III)中のmに相当する値の平均値は0.6であった。
実施例1のフェノール樹脂(1)276g(水酸基当量276g/当量)をフェノール樹脂(1’)262g(水酸基当量は262g/当量)に変更し、比較製造例2記載と同様の方法でエポキシ樹脂(1’)を380g得た。このエポキシ樹脂(1’)のエポキシ当量は350g/当量であった。
温度計、冷却管、分留管、撹拌器を取り付けたフラスコに、99%メタノールを200g、4,4’−ジヒドロキシジフェニルエーテル404g(2モル)、1,6−ブロモ−ヘキサンを244g(1モル)仕込み、75℃の温度条件下で窒素を吹き込みながら撹拌し溶解した。その後、86%水酸化カリウム65g(1モル)を溶解させた99%エタノール溶液200gを30分間かけて添加し、更に撹拌しながら4時間加熱還流した。その後、室温に冷却して30%硫酸を用いて反応液を中和し、濾過、水洗、乾燥を行い、白色結晶を得た。次いで、温度計、冷却管、分留管、撹拌器を取り付けたフラスコに上記で得られた白色結晶と、エピクロルヒドリン1110g、ジメチルスルホキシド222gを仕込み、内圧を約6kPaまで減圧した後、50℃で還流させながら、49%水酸化ナトリウム122gを5時間かけて滴下した。尚、反応中は水を系外に留去、除去しながら反応を行った。49%水酸化ナトリウムの滴下後、70℃に昇温し、同温度でさらに1時間還流させながら反応させた。反応終了後、メチルイソブチルケトン400gと水450gを加え、副生した塩化カリウム水溶液を棄却した。その後、水400gを用いてジメチルスルホキシドを洗浄除去した後、150℃まで昇温して、エピクロルヒドリンを減圧蒸留回収し、エポキシ当量380g/当量のエポキシ樹脂(2’)を300g得た。
先で得られたフェノール性水酸基含有樹脂(1)及びエポキシ樹脂(1’)、(2’)につき、下記の条件で各種評価試験を行った。結果を表1に示す。
[試験片の作成]
下記表1に記載の配合に従い、先で得たフェノール性水酸基含有樹脂(1)又はフェノールノボラック樹脂(DIC株式会社製「TD−2131」)に、硬化剤としてフェノールノボラック型エポキシ樹脂(DIC株式会社製「N−740」)又は前記エポキシ樹脂(1’)、(2’)と、硬化触媒として2−エチル−4−メチルイミダゾール(2E4MZ)とを配合し、更に無機質充填材として球状アルミナ(平均粒径12.2μm)を400g添加した。これをミキサーで十分に混合した後、100℃の温度条件下で5分間加熱し、冷却後に粉砕した。粉砕物を150℃で1時間、更に175℃で6時間加熱して硬化させ、板厚1.2mmの試験片を得た。試験片中の樹脂量は20質量%である。
熱導率計(京都電子株式会社製「QTM−500」)を用いて非定常熱線法により試験片の熱伝統率を測定した。
[試験片の作成]
下記表1に記載の配合に従い、先で得たフェノール性水酸基含有樹脂(1)又はフェノールノボラック樹脂(DIC株式会社製「TD−2131」)に、硬化剤としてフェノールノボラック型エポキシ樹脂(DIC株式会社製「N−740」)又は前記エポキシ樹脂(1’)、(2’)と、硬化触媒として2−エチル−4−メチルイミダゾール(2E4MZ)とを配合し、更にメチルエチルケトンを加えて不揮発分が58質量%の樹脂組成物を調整した。得られた樹脂組成物を下記条件でプリプレグ化し、これを試験片とした。
基材:100μm 日東紡績株式会社製 プリント配線基板用ガラスクロス「2116」
プライ数:6
銅箔:18μm 日鉱金属株式会社製 TCR箔
プリプレグ化条件:160℃/2分
硬化条件:200℃、2.9MPa、2時間
成形後板厚:0.8mm、樹脂量40%
JIS−K6481に準拠し、ピール強度及び層間剥離強度を測定した。
試験片を25mm×75mmの大きさに切り出し、JIS−K6911に従って、島津製作所株式会社製の「AUTOGRAPH AG−I」を用いて3点曲げ伸び率を測定した。
各サンプルそれぞれ3個ずつ試験片を用意し、121℃プレッシャークッカー試験機に6時間放置した後、288℃半田浴に30秒浸漬し、膨れの有無を目視にて確認した。3つの試験片すべてにつき膨れの無いものを○、3つの試験片のうち一つでも膨れが生じたものを×とした。
[試験片の作成]
下記表1に記載の配合に従い、先で得たフェノール性水酸基含有樹脂(1)又はフェノールノボラック樹脂(DIC株式会社製「TD−2131」)に、硬化剤としてフェノールノボラック型エポキシ樹脂(DIC株式会社製「N−740」)又は前記エポキシ樹脂(1’)、(2’)と、硬化触媒として2−エチル−4−メチルイミダゾール(2E4MZ)とを配合した。これをミキサーで十分に混合した後、100℃の温度条件下で5分間加熱し、冷却後に粉砕した。粉砕物を150℃で1時間、更に175℃で6時間加熱して硬化させ、板厚0.2mmの試験片を得た。
粘弾性測定装置(レオメトリック社製「固体粘弾性測定装置RSA II」、レクタンギュラーテンション法;周波数1Hz、昇温速度3℃/分)を用い、弾性率変化が最大となる(tanδ変化率が最も大きい)温度をガラス転移温度として測定した。
質量が6mgとなる大きさに切り出した試験片を150℃で15分間保持した後、窒素ガスフロー条件下、毎分5℃で昇温し、質量の5%が減少した時の温度で評価した。
Claims (11)
- 前記一般式(I)中、Aで表される直鎖又は分岐のアルキレン基が、炭素原子数2〜8の直鎖又は分岐のアルキレン基であり、lの値が1〜3の範囲である請求項1記載のフェノール性水酸基含有樹脂。
- フェノール性水酸基の水酸基当量が200〜450g/当量の範囲である請求項1又は2記載のフェノール性水酸基含有樹脂。
- 結晶性を有し、走査示差熱分析での融点が20℃から250℃の範囲である請求項1〜3の何れか1項記載のフェノール性水酸基含有樹脂。
- 請求項1〜5の何れか一つに記載のフェノール性水酸基含有樹脂と硬化剤を含有する硬化性樹脂組成物。
- 請求項8記載の硬化性樹脂組成物を硬化させて得られる硬化物。
- 請求項1〜5の何れか一つに記載のフェノール性水酸基含有樹脂、硬化剤、及び無機質充填剤を含有し、前記無機質充填剤の割合が20〜95質量%の範囲にある放熱樹脂材料。
- 前記無機質充填剤が、窒化ホウ素、酸化アルミニウム又は窒化アルミニウムである請求項10記載の放熱樹脂材料。
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