JP5896693B2 - リン及び窒素含有エポキシ樹脂 - Google Patents
リン及び窒素含有エポキシ樹脂 Download PDFInfo
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- JP5896693B2 JP5896693B2 JP2011253863A JP2011253863A JP5896693B2 JP 5896693 B2 JP5896693 B2 JP 5896693B2 JP 2011253863 A JP2011253863 A JP 2011253863A JP 2011253863 A JP2011253863 A JP 2011253863A JP 5896693 B2 JP5896693 B2 JP 5896693B2
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- JP
- Japan
- Prior art keywords
- epoxy resin
- phosphorus
- molecular weight
- nitrogen
- curing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 229920000647 polyepoxide Polymers 0.000 title claims description 164
- 239000003822 epoxy resin Substances 0.000 title claims description 163
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 65
- 239000011574 phosphorus Substances 0.000 title claims description 62
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 50
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 13
- 229920003986 novolac Polymers 0.000 claims description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- -1 phosphorus compound Chemical class 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 28
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 26
- 229920005989 resin Polymers 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 238000009826 distribution Methods 0.000 claims description 20
- 239000004593 Epoxy Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 10
- 238000005227 gel permeation chromatography Methods 0.000 claims description 9
- 238000011088 calibration curve Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 66
- 238000001723 curing Methods 0.000 description 31
- 229910000831 Steel Inorganic materials 0.000 description 24
- 239000010959 steel Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 20
- 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 20
- 238000003786 synthesis reaction Methods 0.000 description 20
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- 238000006243 chemical reaction Methods 0.000 description 14
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- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 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 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 9
- 150000003018 phosphorus compounds Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 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 7
- 239000003054 catalyst Substances 0.000 description 7
- 229930003836 cresol Natural products 0.000 description 7
- 239000005011 phenolic resin Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 150000004780 naphthols Chemical class 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 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 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N beta-hydroxynaphthyl Natural products C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 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
- 239000000835 fiber Substances 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- HPUOAJPGWQQRNT-UHFFFAOYSA-N pentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1 HPUOAJPGWQQRNT-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- QLAGHGSFXJZWKY-UHFFFAOYSA-N triphenylborane;triphenylphosphane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QLAGHGSFXJZWKY-UHFFFAOYSA-N 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
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
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- 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
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- 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
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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Description
(1)一般式(1)で示されるリン化合物とシアヌル酸とエポキシ樹脂(a)を反応して得られるリン及び窒素を分子内に含有するエポキシ樹脂(A)において、エポキシ樹脂(a)としてゲルパーミエーションクロマトグラフィーにおける測定において二核体含有率が15面積%以下、三核体含有率が15面積%〜60面積%であり、数平均分子量が350〜700である分子量分布を持つノボラック型エポキシ樹脂(b)を必須として用いることを特徴とするリン及び窒素を分子内に含有するエポキシ樹脂(A)、
(ゲルパーミエーションクロマトグラフィー測定条件)
東ソー株式会社製 TSKgelG4000HXL、TSKgelG3000HXL、TSKgelG2000HXLを直列に備えたものを使用し、カラム温度は40℃にした。また、溶離液にはテトラヒドロフランを用い、1ml/minの流速とし、検出器はRI(示差屈折計)検出器を用いた。サンプル0.1gを10 mlのTHFに溶解した。標準ポリスチレンによる検量線により数平均分子量を測定する。
(2)上記(1)記載のリン及び窒素を分子内に含有するエポキシ樹脂(A)と硬化剤を必須成分とし、エポキシ樹脂(A)のエポキシ基1当量に対して硬化剤の官活性基を0.4当量〜2.0当量を配合してなるエポキシ樹脂組成物、
(3)上記(2)記載のエポキシ樹脂組成物を基材に含浸してなるプリプレグ、
(4)上記(2)記載のエポキシ樹脂組成物を硬化してなるエポキシ樹脂硬化物、
(5)上記(2)記載のエポキシ樹脂組成物を硬化してなる積層板、
に関する。
実施例及び比較例で合成されたエポキシ樹脂のエポキシ当量はJIS K 7236にて測定を行った。
ガラス転移温度TMA:熱機械分析装置(セイコーインスツルメンツ株式会社製 EXSTAR6000 TMA/SS120U)にて5℃/分の昇温条件で測定を行った時のTMA外挿値の温度で表した。
YDPN-638(新日鐵化学株式会社製 フェノールノボラック型エポキシ樹脂、ゲルパーミエーションクロマトグラフィーによる測定で二核体含有率22.1面積%、三核体含有率10.7面積%、数平均分子量463、重量平均分子量1003、分散度2.17、エポキシ当量176g/eq)。
YDF-170(新日鐵化学株式会社製 ビスフェノールF型エポキシ樹脂 エポキシ当量170g/eq)。
YDF-2001(新日鐵化学株式会社製 ビスフェノールF型エポキシ樹脂 エポキシ当量469g/eq)。
攪拌装置、温度計、冷却管、窒素ガス導入装置を備えた4つ口のガラス製セパラブルフラスコに、フェノール 2500部、シュウ酸二水和物 7.5部を仕込み、窒素ガスを導入しながら攪拌を行い、加熱を行って昇温した。37.4%ホルマリン 474.1部を80℃で滴下を開始し、30分で滴下を終了した。更に反応温度を92℃に保ち3時間反応を行った。昇温を行い反応生成水を系外に除去しながら110℃まで昇温した。残存フェノールを160℃にて減圧下回収を行い、フェノールノボラック樹脂を得た。更に温度を上げて二核体の一部を回収した。得られたフェノールノボラック樹脂の二核体含有率はゲルパーミエーションクロマトグラフィーによる測定で10面積%であった。
合成例1と同様な装置に、合成例1のフェノールノボラック樹脂 665.8部、エピクロロヒドリン 2110.8部、水 17部を仕込み、攪拌しながら50℃まで昇温した。49%水酸化ナトリウム水溶液 14.2部を仕込み3時間反応を行った。64℃まで昇温し、水の還流が起きる程度に減圧を引き、49%水酸化ナトリウム水溶液 457.7部を3時間かけて滴下し反応をおこなった。温度を70℃まで上げ脱水を行い、温度を135℃として残存するエピクロロヒドリンを回収した。常圧に戻し、MIBK 1232部を加えて溶解した。イオン交換水1200部を加え、攪拌静置して副生した食塩を水に溶解して除去した。次に49%水酸化ナトリウム水溶液 37.4部を仕込み80℃で90分間攪拌反応して精製反応を行った。MIBKを追加、水洗を数回行いイオン性不純物を除去した。溶剤を回収し、ノボラック型エポキシ樹脂を得た。ゲルパーミエーションクロマトグラフィーによる測定で二核体含有率9面積%、三核体含有率37.0面積%、数平均分子量440、重量平均分子量605、分散度1.38、エポキシ当量176g/eqであった。
合成例1と同様な装置に合成例2のフェノールノボラック型エポキシ樹脂 859部、HCA(三光株式会社製 9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイド リン含有率14.2重量%)134部、シアヌル酸(東京化成工業株式会社製)8部を仕込み、窒素ガスを導入しながら攪拌を行い、加熱を行って昇温した。130℃にてトリフェニルホスフィンを触媒として0.14部を添加して160℃で3時間反応を行った。得られたエポキシ樹脂のエポキシ当量は249g/eq、リン含有率は1.9%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂 873部、HCA 120部とした以外は実施例1と同様な操作を行なった。得られたエポキシ樹脂のエポキシ当量は240g/eq、リン含有率は1.7%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂 743部、HCA 120部とした以外は実施例1と同様な操作を行なった。反応終了後、YDF-170 130部を添加し、均一になるまで攪拌を行なった。得られたエポキシ樹脂のエポキシ当量は236g/eq、リン含有率は1.7%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂 759部、HCA 134部とした以外は実施例1と同様な操作を行なった。反応終了後、YDF-2001 100部を添加し、均一になるまで攪拌を行なった。得られたエポキシ樹脂のエポキシ当量は273g/eq、リン含有率は1.9%であった。結果を表1にまとめる。
合成例1と同様な装置に合成例2のフェノールノボラック型エポキシ樹脂 842部、HCA 100部、HCA-HQ 50部、シアヌル酸 8部を仕込み、窒素ガスを導入しながら攪拌を行い、加熱を行って昇温した。130℃にてトリフェニルホスフィンを触媒として0.15部を添加して160℃で3時間反応を行った。得られたエポキシ樹脂のエポキシ当量は265g/eq、リン含有率は1.9%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂の代わりにYDPN-638 803部、HCA 197部、シアヌル酸 0部とした以外は実施例1と同様な操作を行なった。得られたエポキシ樹脂のエポキシ当量は283g/eq、リン含有率は2.8%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂の代わりにYDPN-638 817部、HCA 183部、シアヌル酸 0部とした以外は実施例1と同様な操作を行なった。得られたエポキシ樹脂のエポキシ当量は275g/eq、リン含有率は2.6%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂の代わりにYDPN-638 824部、HCA 176部、シアヌル酸 0部とした以外は実施例1と同様な操作を行なった。得られたエポキシ樹脂のエポキシ当量は251g/eq、リン含有率は2.5%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂 859部、HCA 141部、シアヌル酸 0部とした以外は実施例1と同様な操作を行なった。得られたエポキシ樹脂のエポキシ当量は236g/eq、リン含有率は2.0%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂 866部、HCA 134部、シアヌル酸 0部とした以外は実施例1と同様な操作を行なった。得られたエポキシ樹脂のエポキシ当量は234g/eq、リン含有率は1.9%であった。結果を表1にまとめる。
合成例2のフェノールノボラック型エポキシ樹脂 880部、HCA 120部、シアヌル酸 0部とした以外は実施例1と同様な操作を行なった。得られたエポキシ樹脂のエポキシ当量は226g/eq、リン含有率は1.7%であった。結果を表1にまとめる。
実施例1〜実施例5、比較例1〜比較例6のエポキシ樹脂と、硬化剤としてジシアンジアミドを表2の処方で配合し、メチルエチルケトン、プロピレングリコールモノメチルエーテル、ジメチルホルムアミドなどの溶剤に溶解してエポキシ樹脂組成物を得た。
Claims (5)
- 一般式(1):
R1及びR2は炭化水素基を表し、同一であっても異なっていてもよく、リン原子と共にR1,R2が環状構造をとってもよく、
nは0または1を表し、そして
Xは水素原子又は一般式2:
で示されるリン化合物とシアヌル酸とエポキシ樹脂(a)を反応して得られるリン及び窒素を分子内に含有するエポキシ樹脂(A)において、前記エポキシ樹脂(a)が、下記条件下でのゲルパーミエーションクロマトグラフィーにおける測定において二核体含有率が15面積%以下、三核体含有率が15面積%〜60面積%であり、数平均分子量が350〜700である分子量分布を持つノボラック型エポキシ樹脂(b)である、ことを特徴とするリン及び窒素を分子内に含有するエポキシ樹脂(A)。
(ゲルパーミエーションクロマトグラフィー測定条件)
東ソー株式会社製 TSKgelG4000HXL、TSKgelG3000HXL、TSKgelG2000HXLを直列に備えたものを使用し、カラム温度は40℃にし、また、溶離液にはテトラヒドロフランを用い、1ml/minの流速とし、検出器はRI(示差屈折計)検出器を用い、サンプル0.1gを10 mlのTHFに溶解する。標準ポリスチレンによる検量線により数平均分子量を測定する。 - 請求項1に記載のリン及び窒素を分子内に含有するエポキシ樹脂(A)と硬化剤を必須成分とし、エポキシ樹脂(A)のエポキシ基1当量に対して硬化剤の官活性基を0.4当量〜2.0当量を配合してなるエポキシ樹脂組成物。
- 請求項2に記載のエポキシ樹脂組成物を基材に含浸してなるプリプレグ。
- 請求項2に記載のエポキシ樹脂組成物を硬化してなるエポキシ樹脂硬化物。
- 請求項2に記載のエポキシ樹脂組成物を硬化してなる積層板。
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JP2011253863A JP5896693B2 (ja) | 2011-11-21 | 2011-11-21 | リン及び窒素含有エポキシ樹脂 |
CN201210128831.8A CN102757547B (zh) | 2011-04-27 | 2012-04-27 | 含磷和氮的环氧树脂 |
TW101139197A TWI538929B (zh) | 2011-11-21 | 2012-10-24 | 含有磷與氮之環氧樹脂 |
KR1020120130025A KR101922732B1 (ko) | 2011-11-21 | 2012-11-16 | 인 및 질소 함유 에폭시 수지 |
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KR20210047861A (ko) * | 2018-08-27 | 2021-04-30 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 인 함유 에폭시 수지, 에폭시 수지 조성물, 프리프레그, 적층판, 회로기판용 재료 및 경화물 |
JP7211829B2 (ja) * | 2019-01-23 | 2023-01-24 | 日鉄ケミカル&マテリアル株式会社 | エポキシ樹脂組成物及びその硬化物 |
JP2020122034A (ja) * | 2019-01-29 | 2020-08-13 | 日鉄ケミカル&マテリアル株式会社 | エポキシ樹脂組成物及びその硬化物 |
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JP2823057B2 (ja) * | 1990-12-20 | 1998-11-11 | 日本化薬株式会社 | エポキシ樹脂の製造方法 |
JP2000080251A (ja) | 1998-09-03 | 2000-03-21 | Matsushita Electric Works Ltd | リン変性難燃性エポキシ樹脂組成物およびその製造方法およびそのリン変性難燃性エポキシ樹脂組成物を用いた成形品および積層体 |
JP2001002759A (ja) * | 1999-06-18 | 2001-01-09 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物及び電気積層板 |
TW513482B (en) | 2001-08-31 | 2002-12-11 | Chang Chun Plastics Co Ltd | Nitrogen-containing flame-retardant epoxy resin and its compositions |
JP2003218517A (ja) | 2002-01-17 | 2003-07-31 | Tokai Rubber Ind Ltd | フレキシブル印刷配線板用耐熱性難燃接着剤組成物およびそれを用いたフレキシブル印刷配線板 |
JP4036011B2 (ja) * | 2002-02-26 | 2008-01-23 | 日立化成工業株式会社 | 難燃性熱硬化樹脂組成物,それを用いたプリプレグ及び電気配線板用積層板 |
JP2006143850A (ja) * | 2004-11-18 | 2006-06-08 | Hitachi Chem Co Ltd | 難燃性樹脂組成物、プリプレグ、金属張積層板 |
JP5676878B2 (ja) * | 2007-05-18 | 2015-02-25 | 新日鉄住金化学株式会社 | 新規な難燃性エポキシ樹脂、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 |
JP5458493B2 (ja) | 2008-01-23 | 2014-04-02 | 日本メクトロン株式会社 | 樹脂組成物 |
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KR20130056180A (ko) | 2013-05-29 |
TWI538929B (zh) | 2016-06-21 |
TW201323467A (zh) | 2013-06-16 |
KR101922732B1 (ko) | 2018-11-27 |
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