JP5334373B2 - 新規なリン含有エポキシ樹脂、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及びその硬化物 - Google Patents
新規なリン含有エポキシ樹脂、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及びその硬化物 Download PDFInfo
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- JP5334373B2 JP5334373B2 JP2007054780A JP2007054780A JP5334373B2 JP 5334373 B2 JP5334373 B2 JP 5334373B2 JP 2007054780 A JP2007054780 A JP 2007054780A JP 2007054780 A JP2007054780 A JP 2007054780A JP 5334373 B2 JP5334373 B2 JP 5334373B2
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- epoxy resin
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- 239000003822 epoxy resin Substances 0.000 title claims description 88
- 229920000647 polyepoxide Polymers 0.000 title claims description 88
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 58
- 239000011574 phosphorus Substances 0.000 title claims description 56
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 52
- 239000000203 mixture Substances 0.000 title claims description 20
- 239000000463 material Substances 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- KJCVRFUGPWSIIH-UHFFFAOYSA-N alpha-naphthol Natural products C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 9
- -1 phosphorus compound Chemical class 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- 239000003566 sealing material Substances 0.000 claims description 7
- JWAZRIHNYRIHIV-UHFFFAOYSA-N beta-hydroxynaphthyl Natural products C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 239000008393 encapsulating agent Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 150000002430 hydrocarbons Chemical group 0.000 claims 6
- 238000010125 resin casting Methods 0.000 claims 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 30
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000004593 Epoxy Substances 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- 238000005266 casting Methods 0.000 description 6
- 239000012778 molding material Substances 0.000 description 6
- 150000002903 organophosphorus compounds Chemical class 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 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 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- 238000010292 electrical insulation Methods 0.000 description 3
- 239000012772 electrical insulation material Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 150000004053 quinones Chemical group 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- LLOXZCFOAUCDAE-UHFFFAOYSA-N 2-diphenylphosphorylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(P(=O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LLOXZCFOAUCDAE-UHFFFAOYSA-N 0.000 description 1
- FEYSBSJNCSKHJC-UHFFFAOYSA-N 2-diphenylphosphorylnaphthalene-1,4-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C=C1P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 FEYSBSJNCSKHJC-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000004978 cyclooctylene group Chemical group 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- GELSOTNVVKOYAW-UHFFFAOYSA-N ethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 GELSOTNVVKOYAW-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
Classifications
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Laminated Bodies (AREA)
Description
b:1,2,3,4,5,6,7
c:1,2,3
(X)はベンゼン、ナフタレン、アントラセン、フェナントレン、ビフェニルを示す。
(Y)は一般式2〜4を示し、1分子中に少なくとも1個は一般式3または一般式4である。
本発明の一般式(1)で示されるαナフトールアラルキル骨格及び/又はβナフトールアラルキル骨格を有する(以下、単にナフトール骨格と称する場合がある。)新規なリン含有エポキシ樹脂は一般式(7)で示されるエポキシ樹脂と一般式(8)及び/又は一般式(9)で示されるリン化合物類と反応することによって得られる。一般式(7)で示されるエポキシ樹脂としては例えばESN−100シリーズのESN−155、ESN−185V、ESN−175(東都化成株式会社製 βナフトールアラルキル型エポキシ樹脂)、ESN−300シリーズのESN−355、ESN−375(東都化成株式会社製 ジナフトールアラルキル型エポキシ樹脂)、ESN−400シリーズのESN−475V、ESN−485(東都化成株式会社製 αナフトールアラルキル型エポキシ樹脂)が挙げられるが、これらに限定されるものではなく、また、2種類以上使用しても良い。また、物性に影響が出ない範囲で、その他のエポキシ樹脂類を使用しても良い。
〔実施例1〕
〔実施例2〕
〔実施例3〕
得られたエポキシ樹脂に表1に示した割合で硬化剤(DICY)及び硬化促進剤(2E4MZ)を添加し、段落〔0016〕に記載した方法により積層板評価を行った。その結果を表1に示す。
〔実施例4〕
得られたエポキシ樹脂に表1に示した割合で硬化剤(DICY)及び硬化促進剤(2E4MZ)を添加し、段落〔0016〕に記載した方法により積層板評価を行った。その結果を表1に示す。
〔比較例1〕
得られたエポキシ樹脂に表1に示した割合で硬化剤(DICY)及び硬化促進剤(2E4MZ)を添加し、段落〔0016〕に記載した方法により積層板評価を行った。その結果を表1に示す。
〔比較例2〕
得られたエポキシ樹脂に表1に示した割合で硬化剤(DICY)及び硬化促進剤(2E4MZ)を添加し、段落〔0016〕に記載した方法により積層板評価を行った。その結果を表1に示す。
〔比較例3〕
得られたエポキシ樹脂に表1に示した割合で硬化剤(DICY)及び硬化促進剤(2E4MZ)を添加し、段落〔0016〕に記載した方法により積層板評価を行った。その結果を表1に示す。
〔比較例4〕
得られたエポキシ樹脂に表1に示した割合で硬化剤(DICY)及び硬化促進剤(2E4MZ)を添加し、段落〔0016〕に記載した方法により積層板評価を行った。その結果を表1に示す。
〔比較例5〕
得られたエポキシ樹脂33.3重量部とESN−485 66.7重量部を配合して積層板評価を行った。積層板評価結果を表1に示す。
本発明の技術によって合成した新規エポキシ樹脂はリン含有率0.8%で難燃性であり、高い耐熱性と低い吸水率の硬化物を得ることが出来る。この様に本発明の新規リン含有エポキシ樹脂、新規リン含有エポキシ樹脂組成物は低いリン含有率で難燃性を有し、併せて耐熱性・接着性・吸水率等の物性が優れているため、特に電子回路基板に用いられる銅張積層板をはじめとする電気絶縁材料に最適であり、電子部品に用いられる封止材・成形材・注型材・接着剤・フィルム材に適しており、更に電気絶縁塗料用材料としても有効である。
Claims (7)
- 一般式(1)で示されるαナフトールアラルキル骨格及び/又はβナフトールアラルキル骨格を有する新規なリン含有エポキシ樹脂。
b:1,2,3,4,5,6,7
c:1,2,3
(X)はベンゼン、ナフタレン、アントラセン、フェナントレン、ビフェニルを示す。
(Y)は一般式2〜4を示し、1分子中に少なくとも1個は一般式3または一般式4である。
R1,R2は炭化水素基を示し、直鎖状、分岐鎖状、環状であっても良い。また、R1とR2が結合し、環状構造となっていても良い。
b:1,2,3,4,5,6,7
g:1,2,3
d:0又は1
f:1,2,3,4,5,6
f+e≦ 6
R1,R2は炭化水素基を示し、直鎖状、分岐鎖状、環状であっても良い。また、R1とR2が結合し、環状構造となっていても良い。
(X)はベンゼン、ナフタレン、アントラセン、フェナントレン、ビフェニルを示す。
(Y)は一般式2 〜 4 を示す。
(Z)は一般式5,6 を示す。
R3:は炭化水素基を示し、直鎖状、分岐鎖状、環状であっても良い。
R3:は炭化水素基を示し、直鎖状、分岐鎖状、環状であっても良い。 - 一般式(7)で示されるαナフトールアラルキル骨格及び/又はβナフトールアラルキル骨格を有するエポキシ樹脂類と一般式(8)及び/ 又は一般式(9)で示されるリン化合物類とを反応して得られる請求項1記載の新規リン含有エポキシ樹脂。
b:1,2,3,4,5,6,7
c:1,2,3
(X)はベンゼン、ナフタレン、アントラセン、フェナントレン、ビフェニルを示す。
R1,R2は炭化水素基を示し、直鎖状、分岐鎖状、環状であっても良い。また、R1とR2が結合し、環状構造となっていても良い。
R1,R2は炭化水素基を示し、直鎖状、分岐鎖状、環状であっても良い。また、R1とR2が結合し、環状構造となっていても良い。
(Z)は一般式5,6を示す。 - 請求項1又は2のリン含有エポキシ樹脂に硬化剤を配合してなるリン含有エポキシ樹脂組成物。
- 請求項3記載のリン含有エポキシ樹脂組成物を用いることを特徴とするエポキシ樹脂積層物。
- 請求項3記載のリン含有エポキシ樹脂組成物を用いることを特徴とするエポキシ樹脂封止材。
- 請求項3記載のリン含有エポキシ樹脂組成物を用いることを特徴とするエポキシ樹脂注型材。
- 請求項3に記載のエポキシ樹脂組成物、請求項4に記載のエポキシ樹脂積層物、請求項5に記載のエポキシ樹脂封止材または請求項6に記載のエポキシ樹脂注型材のいずれかを硬化して得られるリン含有エポキシ樹脂硬化物。
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JP2007054780A JP5334373B2 (ja) | 2007-03-05 | 2007-03-05 | 新規なリン含有エポキシ樹脂、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及びその硬化物 |
TW97107296A TWI457358B (zh) | 2007-03-05 | 2008-03-03 | A novel phosphorus-containing epoxy resin, an epoxy resin composition containing the epoxy resin as an essential component and a hardened product |
CN200880007011.5A CN101679601B (zh) | 2007-03-05 | 2008-03-04 | 含磷环氧树脂、以该环氧树脂作为必须成分的环氧树脂组合物及其固化物 |
US12/449,918 US8057902B2 (en) | 2007-03-05 | 2008-03-04 | Epoxy phosphorous-containing resin, epoxy resin composition essentially containing the epoxy resin, and cured product of the epoxy resin composition |
EP08721664.4A EP2123688A4 (en) | 2007-03-05 | 2008-03-04 | A NEW PHOSPHORUS-BASED EPOXY RESIN, EPOXY RESIN COMPOSITION, ESPECIALLY CONTAINING THE EPOXY RESIN, AND CURED PRODUCT OF THE EPOXY RESIN COMPOSITION |
PCT/JP2008/054248 WO2008108485A1 (ja) | 2007-03-05 | 2008-03-04 | 新規なリン含有エポキシ樹脂、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及びその硬化物 |
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US (1) | US8057902B2 (ja) |
EP (1) | EP2123688A4 (ja) |
JP (1) | JP5334373B2 (ja) |
CN (1) | CN101679601B (ja) |
TW (1) | TWI457358B (ja) |
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JP5376767B2 (ja) * | 2007-03-26 | 2013-12-25 | 新日鉄住金化学株式会社 | 新規熱可塑性ポリヒドロキシポリエーテル樹脂及び、それを配合した樹脂組成物 |
KR101055683B1 (ko) | 2008-12-26 | 2011-08-09 | 제일모직주식회사 | 신규한 포스포네이트계 화합물 및 이를 포함하는 난연성 스티렌계 수지 조성물 |
KR101095225B1 (ko) * | 2009-04-23 | 2011-12-20 | 삼성전기주식회사 | 인쇄회로기판용 수지 조성물 및 이를 이용한 인쇄회로기판 |
JP5341679B2 (ja) * | 2009-08-31 | 2013-11-13 | 株式会社日立製作所 | 半導体装置 |
JP5579008B2 (ja) * | 2010-09-29 | 2014-08-27 | 新日鉄住金化学株式会社 | リン含有エポキシ樹脂 |
JP5911700B2 (ja) * | 2011-11-11 | 2016-04-27 | 新日鉄住金化学株式会社 | 難燃性エポキシ樹脂及び該エポキシ樹脂を必須成分とする組成物、硬化物 |
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JPH0617440B2 (ja) | 1989-05-30 | 1994-03-09 | 新日鐵化学株式会社 | 新規エポキシ樹脂及びその製造法 |
JPH0390075A (ja) | 1989-09-01 | 1991-04-16 | Nippon Steel Chem Co Ltd | エポキシ樹脂及びその中間体並びにその製造法 |
JP3613724B2 (ja) * | 1997-09-09 | 2005-01-26 | 東都化成株式会社 | リン含有エポキシ樹脂組成物 |
JP3533973B2 (ja) * | 1998-01-27 | 2004-06-07 | 東都化成株式会社 | リン含有エポキシ樹脂組成物 |
JP3400363B2 (ja) * | 1998-10-21 | 2003-04-28 | 住友ベークライト株式会社 | 難燃性樹脂組成物、これを用いたプリプレグ及び積層板 |
JP3642403B2 (ja) * | 1999-02-23 | 2005-04-27 | 大日本インキ化学工業株式会社 | 難燃性エポキシ樹脂組成物及び難燃性エポキシ樹脂の製造方法 |
JP3659842B2 (ja) * | 1999-08-09 | 2005-06-15 | 住友ベークライト株式会社 | 積層板用難燃性樹脂組成物、プリプレグ及び積層板 |
US6486242B1 (en) * | 1999-04-20 | 2002-11-26 | Sumitomo Bakelite Company Limited | Flame-retardant resin composition and prepreg and laminate using the same |
JP3412585B2 (ja) * | 1999-11-25 | 2003-06-03 | 松下電工株式会社 | プリント配線板及び多層プリント配線板の製造に用いられるプリプレグ用エポキシ樹脂組成物、プリプレグ、多層プリント配線板 |
TW587094B (en) * | 2000-01-17 | 2004-05-11 | Sumitomo Bakelite Co | Flame-retardant resin composition comprising no halogen-containing flame retardant, and prepregs and laminates using such composition |
JP5126923B2 (ja) * | 2000-03-31 | 2013-01-23 | Dic株式会社 | エポキシ樹脂組成物 |
JP4588834B2 (ja) * | 2000-04-06 | 2010-12-01 | パナソニック電工株式会社 | リン含有エポキシ樹脂組成物及び、該リン含有エポキシ樹脂を用いる難燃性の樹脂シート、樹脂付き金属箔、プリプレグ及び積層板、多層板 |
JP4837175B2 (ja) * | 2001-02-23 | 2011-12-14 | 新日鐵化学株式会社 | リン含有エポキシ樹脂組成物 |
US20030073781A1 (en) * | 2001-08-14 | 2003-04-17 | Chang Chun Plastics Co., Ltd. | Phosphorus-containing resin and flame retardant resin composition containing the same |
JP2004123859A (ja) | 2002-10-01 | 2004-04-22 | Nippon Steel Chem Co Ltd | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物 |
CN1989166B (zh) * | 2004-11-30 | 2010-04-28 | 松下电工株式会社 | 预浸料用环氧树脂组合物、预浸料及多层印刷电路板 |
JP4465257B2 (ja) | 2004-12-07 | 2010-05-19 | 新日鐵化学株式会社 | ナフトール樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及びその硬化物 |
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WO2008108485A1 (ja) | 2008-09-12 |
EP2123688A1 (en) | 2009-11-25 |
TW200902580A (en) | 2009-01-16 |
US8057902B2 (en) | 2011-11-15 |
JP2008214513A (ja) | 2008-09-18 |
TWI457358B (zh) | 2014-10-21 |
EP2123688A4 (en) | 2013-12-18 |
US20100093928A1 (en) | 2010-04-15 |
CN101679601B (zh) | 2014-06-25 |
CN101679601A (zh) | 2010-03-24 |
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