CN104379626B - Phosphorous epoxy resin and using the epoxy resin as the composition of essential component, solidfied material - Google Patents
Phosphorous epoxy resin and using the epoxy resin as the composition of essential component, solidfied material Download PDFInfo
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- CN104379626B CN104379626B CN201380030849.7A CN201380030849A CN104379626B CN 104379626 B CN104379626 B CN 104379626B CN 201380030849 A CN201380030849 A CN 201380030849A CN 104379626 B CN104379626 B CN 104379626B
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- Prior art keywords
- epoxy resin
- phosphorous
- area
- molecular weight
- composition
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 181
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 181
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims description 33
- 239000000463 material Substances 0.000 title description 11
- -1 phosphorus compound Chemical class 0.000 claims abstract description 71
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 41
- 239000011574 phosphorus Substances 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 238000009826 distribution Methods 0.000 claims abstract description 20
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 10
- 238000005259 measurement Methods 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 229920003986 novolac Polymers 0.000 claims description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 43
- 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 28
- 229910000831 Steel Inorganic materials 0.000 description 23
- 239000010959 steel Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 18
- 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 17
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 15
- 150000002924 oxiranes Chemical class 0.000 description 15
- 229920001568 phenolic resin Polymers 0.000 description 15
- 239000005011 phenolic resin Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000000191 1,4-naphthoquinones Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 229940106691 bisphenol a Drugs 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000010426 asphalt Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 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 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 150000004782 1-naphthols Chemical class 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
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 2
- 150000008614 2-methylimidazoles Chemical class 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
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- XDKUKGIJDNUFGK-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CN=C[N]1 XDKUKGIJDNUFGK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- BXJGUBZTZWCMEX-UHFFFAOYSA-N dimethylhydroquinone Natural products CC1=C(C)C(O)=CC=C1O BXJGUBZTZWCMEX-UHFFFAOYSA-N 0.000 description 2
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- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 235000012254 magnesium hydroxide Nutrition 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N methyl resorcinol Natural products COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
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- INZDTEICWPZYJM-UHFFFAOYSA-N 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=C(CCl)C=C1 INZDTEICWPZYJM-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- NCIAGQNZQHYKGR-UHFFFAOYSA-N naphthalene-1,2,3-triol Chemical compound C1=CC=C2C(O)=C(O)C(O)=CC2=C1 NCIAGQNZQHYKGR-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- OXKVZHIHRSTGAN-UHFFFAOYSA-N naphthalene;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 OXKVZHIHRSTGAN-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 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
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 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
- 239000002245 particle Substances 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
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-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
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical class Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
- 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
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1488—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing phosphorus
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- 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
- C08G59/3272—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/04—Epoxynovolacs
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/02—Composition of the impregnated, bonded or embedded layer
- B32B2260/021—Fibrous or filamentary layer
- B32B2260/023—Two or more layers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/07—Parts immersed or impregnated in a matrix
- B32B2305/076—Prepregs
-
- C—CHEMISTRY; METALLURGY
- 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
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2363/04—Epoxynovolacs
-
- 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
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0104—Properties and characteristics in general
- H05K2201/012—Flame-retardant; Preventing of inflammation
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
The present invention provides a kind of epoxy resin, has the characteristic that heat resistance further increases while keeping previous bonding force；A kind of phosphorous epoxy resin (A), it is characterized in that, it is epoxy resin phosphorous obtained from phosphorus compound, naphtoquinone compounds and the epoxy resin (a) for indicating general formula (1) are reacted as essential component, wherein, epoxy resin (a) is in the measurement of gel permeation chromatography, the phenol aldehyde type epoxy resin for the molecular weight distribution that with two nucleome containing ratios be 15 area % or less, three nucleome containing ratios are 15 area of area % ~ 60 %, number-average molecular weight is 350 ~ 700.
Description
Technical field
The present invention relates in molecular skeleton containing phosphorus atoms, the fire-retarded epoxy resin that is halogen-free, and with this
Composition epoxy resin of the epoxy resin as essential component, further relates to the ring for forming the epoxy resin composition
Oxygen resin cured matter；The present invention provides the epoxy resin for being suitble to following purposes: prepreg used in circuit substrate covers copper lamination
Thin-film material used in plate or electronic component, sealing material, moulding material, cast-molding material, bonding agent, electrically-insulating paint need
Want the composite material of anti-flammability, powder coating etc..
Background technique
The flame-retarded of epoxy resin was carried out by halogenation in the past, and representative is using tetrabromobisphenol A as the bromine of raw material
Change epoxy resin.But when using halogenated epoxy resin, there is following problem: discovery is in the burning of solidfied material due to thermal decomposition
React and generate the halide of strong toxicity.In this regard, Recent study is mentioned using the flame-retarded technology that is halogen-free of phosphorus compound
Go out such as patent document 1 ~ phosphorous epoxy resin disclosed in Patent Document 7, phosphorous phenolic resin.
Patent document 1, phosphorous epoxy resin disclosed in Patent Document 2 are turned although bonding force is high with vitrifying
Temperature is that the heat resistance of representative is insufficient；Phosphorous epoxy resin disclosed in Patent Document 3, although improving glass transition
Temperature, but be difficult to take into account bonding force.In addition, phosphorous epoxy resin disclosed in Patent Document 4, by using naphtoquinone compounds
To realize the raising of high bonding force and high-fire resistance.In turn, in patent document 5, by and with specific 2 functional epoxy resins,
High bonding force and high-fire resistance are further increased to realize；About phosphorous epoxy resin disclosed in Patent Document 6, also grind
The raising of bonding force and high-fire resistance is studied carefully.But for glass transition temperature, the requirement with more height, it is desirable that tieing up
It is improved while holding bonding force.
The phosphorous epoxy resin obtained by the flame-retarded gimmick of phosphorus compound is difficult to take into account high-fire resistance and high bonding
Power, if carried out to improve heat resistance it is multiple functionalized if bonding force reduce；If carrying out phosphatization to improve bonding force
Close the 2 functionalizations then heat resistance reduction of object.In this regard, being proposed in patent document 5, by using spy in the range of 20% ~ 45%
2 fixed functional epoxy resins, can further improve high-fire resistance and high bonding force.
Existing technical literature
Patent document
Patent document 1: 04 No. 11662 bulletins of Japanese Unexamined Patent Publication
Patent document 2: 2000 No. 309623 bulletins of Japanese Unexamined Patent Publication
Patent document 3: 11 No. 166035 bulletins of Japanese Unexamined Patent Publication
Patent document 4: 11 No. 279258 bulletins of Japanese Unexamined Patent Publication
Patent document 5: Japanese Patent No. 4588834
Patent document 6: 2001 No. 123049 bulletins of Japanese Unexamined Patent Publication
Patent document 7: 2003 No. 040969 bulletins of Japanese Unexamined Patent Publication.
Summary of the invention
Technical problems to be solved by the inivention
Recently, in circuit substrate etc., in order to Reflow Soldering temperature rising, ensure long-term reliability, heat resistance, particularly
Glass transition temperature requires to further increase.The technical problem to be solved in the present invention is to provide a kind of epoxy resin, have
The characteristic that heat resistance further increases while keeping bonding force.
Solve the means of technical problem
In order to solve the above-mentioned technical problem, the inventors discovered that, using having specific molecular weight point in the epoxy
Phosphorous epoxy resin obtained from phenol aldehyde type (the ノ ボ ラ ッ Network type) epoxy resin and phosphorus compound, naphtoquinone compounds of cloth, can be with
Heat resistance is improved while maintaining high bonding force, and then finds that anti-flammability is good, so as to complete the present invention.
That is, the method is characterized in that,
(1) phosphorous epoxy resin (A), which is characterized in that it is the phosphorus compound for indicating general formula (1), naphtoquinone compounds
Phosphorous epoxy resin obtained from being reacted with epoxy resin (a) as essential component, wherein epoxy resin (a) be
In the measurement of following gel permeation chromatographies, there is two nucleomes (two nucleomes) containing ratio to contain for 15 area % or less, three nucleomes
Rate is the phenol aldehyde type epoxy resin of 15 area of area % ~ 60 %, the molecular weight distribution that number-average molecular weight is 350 ~ 700；
(gel permeation chromatography determination condition)
Using having (Dong ソ ー Co., Ltd., TOSOH Co., Ltd in-linely) TSKgelG4000HXL processed,
The equipment of TSKgelG3000HXL, TSKgelG2000HXL make 40 DEG C of column temperature.Eluent uses tetrahydrofuran (THF), flow velocity
For 1ml/min, detector uses RI (differential refractometer) detector.Measurement is that sample 0.1g is dissolved in 10ml's with sample
THF.Two nucleome containing ratios and three nucleome containing ratios are calculated using resulting chromatography, are surveyed using the standard curve of standard polystyren
Fixed number average molecular weight；
(R1 and R2 indicates alkyl in formula, can be the same or different, R1, R2 can be formed together ring-type with phosphorus atoms
Structure.N indicates 0 or 1.)；
(2) phosphorous composition epoxy resin, wherein the phosphorous epoxy resin (A) recorded with above-mentioned (1) and solidification
Agent cooperates 0.3 equivalent of active group of curing agent relative to 1 equivalent of epoxy group of phosphorous epoxy resin (A) as essential component
~ 1.5 equivalents form；
(3) epoxy resin cured product is that the phosphorous epoxy resin composition for recording above-mentioned (2) forms；
(4) prepreg is to be impregnated with the phosphorous composition epoxy resin of above-mentioned (2) record to form in the substrate；
(5) laminated plate is that the phosphorous epoxy resin composition for recording above-mentioned (2) forms；
(6) circuit substrate is that the phosphorous epoxy resin composition for recording above-mentioned (2) forms.
Invention effect
The present invention is, by that will have the phenol aldehyde type epoxy resin of specific molecular weight distribution, phosphorus compound and quinone chemical combination
Object epoxy resin phosphorous obtained from being reacted as essential component, by using the phenol with specific molecular weight distribution
Aldehyde type epoxy resin can obtain showing the phosphorous of the solidfied material physical property that glass transition temperature is high while maintaining bonding force
Epoxy resin.In turn, the viscosity of epoxy resin is low, and operational and also good to the impregnability of substrate, anti-flammability is also good.
Detailed description of the invention
Fig. 1 shows gel permeation chromatography (GPC) figures of universal novolac type epoxy resin, that is, YDPN 638.Horizontal axis table
Show elution time, the left longitudinal axis indicates signal strength.The right longitudinal axis indicates number-average molecular weight M with log.By the number of the standard substance used
The measured value of average molecular weight use black circle to draw and as standard curve.Peak shown in A indicates that peak shown in two nucleomes, B indicates three
Nucleome.
Fig. 2 indicates the GPC figure of the phenol aldehyde type epoxy resin of synthesis example 2.Peak shown in A indicates peak table shown in two nucleomes, B
Show three nucleomes.
Specific embodiment
It is described in detail below for embodiments of the present invention.
Epoxy resin (a) used in the present invention is the reaction product of phenols and aldehydes, is to have specific molecular weight point
Polyfunctional phenol aldehyde type epoxy resin obtained from phenolic resin and the epoxyhalopropane reaction of cloth.It, can as the phenols used
It enumerates: phenol, cresols, ethyl -phenol, butylphenol, styrenated phenol, cumenyl phenol, naphthols, catechol, resorcinol, naphthalene
Diphenol, bisphenol-A etc.；As aldehydes, can enumerate formalin (formalin), formaldehyde (formaldehyde), hydroxy benzaldehyde,
Salicylide etc..In addition, substitution aldehydes, uses xyxylene dimethanol (xylylene dimethanol), bis- (chloromethyl) benzene
The aralkyl phenolic resin of (xylylene dichloride), dichloride methyl naphthalene, dichloride methyl biphenyl etc. are also contained in the present invention
Phenolic resin in.By carrying out epoxidation using epoxyhalopropane to above-mentioned phenolic resin, to obtain phenolic aldehyde type ring
Oxygen resin.
It as the concrete example of common phenol aldehyde type epoxy resin, can enumerate: 638 (Nippon Steel's chemistry strain of エ ポ ト ー ト YDPN
Formula commercial firm novolac type epoxy resin), エ ピ コ ー ト 152,154 (Mitsubishi chemical Co., Ltd's line of エ ピ コ ー ト
Type phenol aldehyde type epoxy resin), エ ピ Network ロ Application N 740, エ ピ Network ロ Application N 770,775 (Dainippon Ink Chemicals of エ ピ Network ロ Application N
Novolac type epoxy resin processed), serial (the Nippon Steel Chemical Co., Ltd's Cresol formaldehyde type ring of エ ポ ト ー ト YDCN 700
Oxygen resin), エ ピ Network ロ Application N 660, エ ピ Network ロ Application N 665, エ ピ Network ロ Application N 670, エ ピ Network ロ Application N 673, エ ピ
Network ロ Application N 695 (Dainippon Ink Chemicals's Cresol formaldehyde type epoxy resin), EOCN 1020, EOCN 102S, EOCN 104S
(Nippon Kayaku K. K's Cresol formaldehyde type epoxy resin), エ Port ト ー ト ZX 1071T, 1270 ZX, (the new day of ZX 1342
Iron Chemical Co., Ltd. alkyl phenolic type epoxy resin), エ Port ト ー ト ZX 1247, (the Nippon Steel's chemistry strain formula meeting of GK 5855
Society's preparation of styrene novolac type epoxy resin), エ ポ ト ー ト ZX 1142L (Nippon Steel Chemical Co., Ltd's naphthols phenol
Aldehyde type epoxy resin), ESN 155, ESN 185V, 175 ESN (Nippon Steel Chemical Co., Ltd's Beta Naphthol 99MIN aralkyl type epoxy
Resin), the ESN 355 of the series of ESN 300, (the Nippon Steel Chemical Co., Ltd bisnaphthol aralkyl type epoxy tree of ESN 375
Rouge), the ESN 475V of the series of ESN 400,485 ESN (Nippon Steel Chemical Co., Ltd α naphthols aralkyl-type epoxy resin)
Bis-phenol phenol aldehyde type epoxy resin etc., but these epoxy resin do not have the specific molecular weight distribution in the present invention.
For obtaining the epoxy resin (a) used in the present invention with specific molecular weight distribution, adjusting can be passed through
The molar ratio of phenols and aldehydes, and remove the method for low molecular weight compositions from resulting phenolic resin and obtain.Further, it is also possible to
The phenolic aldehyde obtained using the manufacturing method as shown in patent document 8, patent document 9 (ノ ボ ラ ッ Network) resin is subjected to epoxy
Resinification；
Patent document 8: 2002 No. 194041 bulletins of Japanese Unexamined Patent Publication
Patent document 9: 2007 No. 126683 bulletins of Japanese Unexamined Patent Publication.
For the molar ratio of phenols and aldehydes, the molar ratio using phenols relative to 1 mole of aldehydes is indicated, with 1 or more
Ratio manufactures, but it is mole bigger when, generate a large amount of two nucleomes, three nucleomes；When mole smaller, a large amount of high molecular weight are generated
Body, two nucleomes, three nucleomes tail off.
For obtaining the epoxy resin (a) used in the present invention with specific molecular weight distribution, can be used such as lower section
Method obtains: the method for removing two nucleomes using the dissolution sex differernce of various solvents from resulting phenolic resin class；By two nucleomes
The method etc. for being dissolved in aqueous alkali and removing can also use other well known separation method.
Having specific molecular weight point can be obtained using well known epoxidizing method to the phenolic resin for controlling molecular weight
The phenol aldehyde type epoxy resin of cloth.Alternatively, by removed from commercially available phenol aldehyde type epoxy resin using various methods two nucleomes at
Divide, also the available phenol aldehyde type epoxy resin with specific molecular weight distribution.Other well known separation side can also be used
Method.
With the epoxy resin (a) of specific molecular weight distribution used in the present invention, preferably two nucleome containing ratios are 15
Area % or less, the more preferable 5 area area of % ~ 12 %.By the way that the physical property such as bonding force can be improved containing two a small amount of nucleomes.Three cores
Body containing ratio is preferably 15 area of area % ~ 60 %, more preferably 20 area of area % ~ 50 %.The containing ratio of three nucleomes is less than 15 faces
When product %, heat resistance is easy to be deteriorated；When more than 60 area %, cementability is easy to be deteriorated.It should be noted that about four nucleomes and five nucleomes
Above range does not provide particularly, but total containing ratio of three nucleomes and four nucleomes is preferably 30 area of area % ~ 70 %.Three cores
When total containing ratio of body and four nucleomes is in the range of the 30 area % of area % ~ 70, further improve anti-flammability.It is more than five nucleomes
Containing ratio is preferably 45 area % or less, more preferably 40 area % or less.More than five nucleomes containing ratio if 45 area % with
Under, then it can get the higher solidfied material of bonding force.Number-average molecular weight is preferably 350 ~ 700, more preferably 380 ~ 600.Number is divided equally
When son amount is more than 700, the viscosity of resulting phosphorous epoxy resin (A) is got higher, and may be generated to operability, substrate impregnability
Adverse effect.For utilizing these conditions, so that the reasons why anti-flammability of the phosphorous epoxy resin (A) made improves, recognizes
For be since the elasticity modulus of resulting solidfied material is lower, so that the carbon (チ ャ ー) that generates becomes more strong in burning, band
Carry out higher insulation effect, but invalidated.
The phosphorus compound that general formula used in the present invention (1) indicates, specifically, can enumerate: dimethyl phosphine, diethyl
Phosphine, diphenylphosphine, 9,10 dihydro, 9 oxa-, 10 phospho hetero phenanthrene, 10 oxide (HCA Sanko Co., Ltd. system), dimethyl phosphine
Oxide, diethyl phosphine oxide, dibutyl phosphine oxide, diphenyl phosphine oxide, 1,4 cyclo-octene phosphine oxides, 1,5 rings
Octene phosphine oxide (CPHO Nippon Chemical Ind system) etc..These phosphorus compounds can be used alone can also be with 2 kinds
It is used in mixed way above, is not limited to these.
Naphtoquinone compounds in the present invention can be enumerated: benzoquinones, naphthoquinones, toluiquinone, anthraquinone and their isomers have
The naphtoquinone compounds etc. of hydrocarbyl substituent, can be used alone can also be used in mixed way with two or more, be not limited to these.General formula (1)
The phosphorus compound of expression and the molar ratio of naphtoquinone compounds, preferably phosphorus compound: naphtoquinone compounds=1:1 or less are more preferably
1:0.99 ~ 0.2 is desired for 1:0.98 ~ 0.40.When naphtoquinone compounds become surplus, remain in as unreacted component phosphorous
In epoxy resin (A), therefore physical property is easy to cause to reduce；When being lower than 0.2, heat resistance, anti-flammability may be generated bad
It influences.In addition, can be used after phosphorus compound is reacted with naphtoquinone compounds by purifying the substance after only taking out reacted constituent.
Phosphorous epoxy resin (A) of the invention is the phosphorus compound for indicating general formula (1), naphtoquinone compounds and has specific
The epoxy resin (a) of molecular weight distribution obtained as essential component reaction, but do not have to function and effect of the invention
In the range of influence, other well known common epoxy resin, modifying agent can also be further used.
Phosphorus compound that general formula (1) indicates, naphtoquinone compounds and the epoxy resin (a) with specific molecular weight distribution it is anti-
It can should be carried out using well known method.There are as below methods: after phosphorus compound is reacted with naphtoquinone compounds, and then and epoxy resin
(a) method reacted；After phosphorus compound is reacted in epoxy resin (a) with naphtoquinone compounds, so it is anti-with epoxy resin (a)
The method answered；It is previously obtained the product for reacting phosphorus compound with naphtoquinone compounds, then the method etc. reacted with epoxy resin (a),
To reaction step, there is no particular limitation in the present invention.
Reaction temperature can be the temperature being normally set up in the synthesis of indirect method epoxy resin, be 100 DEG C ~ 250 DEG C, preferably
It is 120 DEG C ~ 200 DEG C.
In reaction, in order to shorten the time, reduce reaction temperature, catalyst can be used.Workable catalyst is without spy
Catalyst usually used in the synthesis of indirect method epoxy resin can be used in other limitation.For example, the uncles such as benzyldimethylamine, 2,4
The phosphines, ethyl triphenyl such as the quaternary ammonium salts such as amine, tetramethyl ammonium chloride, triphenylphosphine, three (2,6 Dimethoxyphenyl) phosphines
The various catalyst such as the imidazoles such as phosphonium bromide Deng phosphonium salts class, 2-methylimidazole, 2-ethyl-4-methylimidazole, can be used alone,
It can also be used in combination with two or more, be not limited to these.It is used for several times further, it is also possible to separate to be divided into.
Catalytic amount is not particularly limited, relative to epoxy resin (a) and can other well known common asphalt mixtures modified by epoxy resin
The total weight of lipid is 5 mass % or less, more preferably 1 mass % or less, further preferably 0.5 mass % or less.Catalytic amount
When more, the auto polymerization reaction of epoxy group is according to circumstances carried out, therefore resin viscosity is got higher, not preferably.
Phosphorus compound, naphtoquinone compounds and the epoxy resin (a) with specific molecular weight distribution that general formula (1) is indicated are anti-
At once, as needed, in the range of not damaging characteristic of the invention, can also and with various epoxy resin modification agent.As
Modifying agent can be enumerated: bisphenol-A, Bisphenol F, bisphenol-A D, tetrabutyl bisphenol-A, quinhydrones, methylnaphthohydroquinone, dimethyl hydroquinone, dibutyl
Quinhydrones, resorcinol, methyl resorcinol, biphenol (ビ Off ェ ノ ー Le), tetramethyl biphenol, dihydroxy naphthlene, dihydroxy
Diphenyl ether, dihydroxy stibene class, linear phenol-aldehyde resin, cresol formaldehyde resin, bisphenol A phenolic resin, two rings penta 2
Alkene phenolic resin, phenol aralkyl resin, naphthol novolac resin, terpene phenolic resin, heavy oil phenol-formaldehyde resin modified, bromination line style
The condensation reaction of various aldehydes such as the various phenols such as phenolic resin, various phenols and hydroxy benzaldehyde, crotonaldehyde, glyoxal and obtain
Polynary phenolic resin, aniline, phenylenediamine, toluidines, dimethylaniline, diethyl toluene diamine, diaminodiphenyl-methane, two
Aminodiphenyl base ethane, diamino-diphenyl propane, diamino-diphenyl ketone, diamino-diphenyl sulfide, diamino hexichol
Base sulfone, bis- (aminophenyl) fluorenes, diamino diethyl-dimethyl diphenyl methane, diamino-diphenyl ether, diaminobenzene formyl
Aniline, benzidine, tolidine, biphenyl tetramine, double aminophenyl anthracenes, double amino-benzene oxygen benzene, double amino
Phenoxyphenyl ether, double amino-benzene oxygen biphenyl, double aminophenoxy phenyl sulfones, double aminophenoxy phenyl propane, diamino
The amine compounds such as naphthalene, are not limited to these, and two or more kinds may be used.
Phosphorus compound, naphtoquinone compounds and the epoxy resin (a) with specific molecular weight distribution that general formula (1) is indicated are anti-
At once, as needed, the degree of characteristic of the present invention can also not damaged and with other various epoxy resins.As can be simultaneously
Epoxy resin, it is specific enumerable: エ ポ ト ー ト YDC 1312, (the Nippon Steel Chemical Co., Ltd's hydrogen manufacturing quinone of ZX 1027
Type epoxy resin), YX 4000 (Mitsubishi chemical Co., Ltd's system) (Nippon Steel Chemical Co., Ltd's bis-phenol type ring of ZX 1251
Oxygen resin), エ ポ ト ー ト YD 127, エ ポ ト ー ト YD 128, エ ポ ト ー ト YD 8125, エ ポ ト ー ト YD 825GS, エ
ポ ト ー ト YD 011, エ ポ ト ー ト YD 900,901 (Nippon Steel Chemical Co., Ltd BPA type ring oxygen of エ ポ ト ー ト YD
Resin), エ ポ ト ー ト YDF 170, エ ポ ト ー ト YDF 8170, エ ポ ト ー ト YDF 870GS, エ ポ ト ー ト YDF 2001
(Nippon Steel Chemical Co., Ltd BPF type epoxy resin), 638 (Nippon Steel Chemical Co., Ltd's system of エ Port ト ー ト YDPN
Novolac type epoxy resin), 701 (Nippon Steel Chemical Co., Ltd's Cresol formaldehyde type asphalt mixtures modified by epoxy resin of エ Port ト ー ト YDCN
Rouge), ZX 1201 (Nippon Steel Chemical Co., Ltd's bisphenol fluorene type epoxy resin), (the Nippon Kayaku K. K's system of NC 3000
Biphenyl aralkyl phenol aldehyde type epoxy resin), EPPN 501H, EPPN 502H (Nippon Kayaku K. K multi-functional epoxy tree
Rouge) ZX 1355 (Nippon Steel Chemical Co., Ltd's naphthalenediol type epoxy resin), ESN 155, ESN 185V, 175 ESN are (new
Day iron Chemical Co., Ltd. Beta Naphthol 99MIN aralkyl-type epoxy resin), ESN 355,375 (Nippon Steel Chemical Co., Ltd of ESN
Bisnaphthol aralkyl-type epoxy resin processed), ESN 475V, 485 ESN (Nippon Steel Chemical Co., Ltd α naphthols aralkyl
Type epoxy resin) etc. by the oxybenzene compounds such as polynary phenolic resin and epoxyhalopropane manufacture epoxy resin, エ Port ト ー ト YH
434, エ ポ ト ー ト YH 434GS (Nippon Steel Chemical Co., Ltd's diaminodiphenyl-methane four glycidyl group ether) etc.
By epoxy resin, (the Nippon Steel Chemical Co., Ltd's dimer acid type epoxy of YD 171 of amine compounds and epoxyhalopropane manufacture
Resin) etc. by carboxylic acids and epoxyhalopropane manufacture epoxy resin etc., but be not limited to these, two or more kinds may be used.
Phosphorus compound, naphtoquinone compounds and the epoxy resin (a) with specific molecular weight distribution that general formula (1) is indicated are anti-
At once, as needed, atent solvent can also be used.Specifically usable hexane, heptane, octane, decane, dimethylbutane, penta
It is the various hydrocarbon such as alkene, hexamethylene, hexahydrotoluene, benzene,toluene,xylene, ethylo benzene, ether, isopropyl ether, butyl ether, two different
Amyl ether, methyl phenyl ether, ethylphenyl ether, amyl phenyl ether, ethyl benzyl ether, dioxanes, methylfuran, tetrahydrofuran etc.
Ethers, methyl cellosolve (methyl cellosolve), methylcellosolve acetate, ethyl cellosolve, cellosolve acetate, second
Glycol isopropyl ether, diethylene glycol dimethyl ether, Methylethyl carbitol, propylene glycol monomethyl ether, dimethylformamide, dimethyl
Sulfoxide etc., but these are not limited to, it can be used in mixed way with two or more.
Phosphorous epoxy resin (A) of the invention, by the phosphorous asphalt mixtures modified by epoxy resin for cooperating the available curability of curing agent
Oil/fat composition.As curing agent, it is logical that various phenolic resin classes, anhydride, amine, hydrazides, acid polyesters etc. can be used
The hardener for epoxy resin being often used, these curing agent can be used only a kind, two or more also can be used.Wherein, as
The curing agent contained in curable epoxy resin composition of the invention, particularly preferred dicyandiamide or phenol system curing agent.This hair
In bright curable epoxy resin composition, the usage amount of curing agent is that functional group, that is, epoxy group 1 relative to epoxy resin is worked as
Amount, the functional group of curing agent are preferably 0.4 ~ 2.0 equivalent, more preferably 0.5 ~ 1.5 equivalent, particularly preferably 0.5 ~ 1.0 equivalent.
Relative to 1 equivalent of epoxy group, when curing agent is less than 0.4 equivalent, or when more than 2.0 equivalent, solidification becomes not exclusively, Ke Nengwu
Method obtains good solidification physical property.
As the concrete example of the phenol system curing agent used in curable epoxy resin composition of the invention, can show
Example: bisphenol-A, Bisphenol F, bisphenol-c, bis-phenol K, bisphenol Z, bisphenol S, bisphenol-A, tetramethyl Bisphenol F, tetramethyl bisphenol S, four
Methyl bisphenol Z, dihydroxydiphenyl sulfide, 4, the bisphenols such as 4 ' thiobis (3 methyl, 6 tert-butyl phenol) and, youngster
Tea phenol, resorcinol, methyl resorcinol, quinhydrones, monomethyl quinhydrones, dimethyl hydroquinone, trimethylhydroquinone, single tert-butyl hydrogen
The hydroxyls such as the dihydroxy benzenes such as quinone, di-tert-butyl hydroquinone class, dihydroxy naphthlene, bishydroxymethyl naphthalene, bishydroxymethyl naphthalene, trihydroxynaphthalene
The phenol such as naphthalenes, linear phenol-aldehyde resin, DC 5 (Nippon Steel Chemical Co., Ltd's cresol formaldehyde resin), naphthol novolac resin
The phenol such as the condensation product of class and/or aphthols and aldehydes, SN 160, SN 395, SN 485 (Nippon Steel Chemical Co., Ltd's system)
Condensation product, the benzene of the condensation product of class and/or aphthols and benzene dimethanol, phenol and/or aphthols and isopropenyl acetophenone
The condensation product etc. of the reactant of phenols and/or aphthols and bicyclopentadiene, phenol and/or aphthols and biphenyl system condensing agent
Oxybenzene compound etc..
It as above-mentioned phenol, can enumerate: phenol, cresols, dimethlbenzene, butylphenol, amyl phenol, nonyl benzene
Phenol, butyl methyl phenol, pseudocuminol, phenylphenol etc.；It as aphthols, can enumerate: 1 naphthols, 2 naphthols etc..
It, can example as aldehydes: formaldehyde, acetaldehyde, propionic aldehyde, butyraldehyde, valeral, hexanal, benzaldehyde, chloral, bromal, second two
Aldehyde, malonaldehyde, butanedial, glutaraldehyde, hexandial, dialdehyde in heptan, decanedial, methacrylaldehyde, crotonaldehyde, salicylide, phthaladehyde, hydroxyl
Benzaldehyde etc..It, can example as biphenyl system condensing agent: bis- (methylol) biphenyl, bis- (methoxy) biphenyl, bis- (ethyoxyls
Methyl) biphenyl, bis- (chloromethyl) biphenyl etc..
As can be arranged in other well known common curing agent used in curable epoxy resin composition of the invention
Lift: methyl tetrahydrophthalic anhydride, hexahydrophthalic anhydride, pyromellitic dianhydride, phthalic anhydride, trimellitic anhydride,
The anhydrides such as methyl nadic acid, diethylenetriamines, trien, m-xylene diamine, isophorone diamine, diamino
The condensation of the acids and polyamines class such as base diphenyl methane, diamino diphenyl sulfone, diamino-diphenyl ether, dicyandiamide, dimeric dibasic acid
Amine compounds such as object, that is, daiamid etc..
In turn, as the polymerization for causing epoxy group and make cured curing agent, it can example: the phosphine compounds such as triphenylphosphine,
4-phenyl phosphonium bromide Deng phosphonium salts, 2 methylimidazoles, 2 phenylimidazoles, 2 ethyl, 4 methylimidazole, 2 undecyl imidazoles, 1
Salt, that is, imidazole salt, the benzyl of the imidazoles such as 2 methylimidazole of cyano ethyl and they and trimellitic acid, isocyanuric acid, boron etc.
The quaternary ammonium salts, diaza two such as amines, the trimethyl ammonium chlorides such as base dimethyl amine, 2,4,6 3 (dimethylaminomethyl) phenol
The complexing of 3 boron fluoride of salt and amine, ether compound etc. of cycle compound and they and phenols, linear phenol-aldehyde resin class etc.
Object, Fang Xiang Zu Phosphonium or salt compounded of iodine etc..These curing agent may be used alone, two or more kinds can also be used.
The match ratio of common epoxy curing agent known in others used in composition epoxy resin of the invention
Example is, relative to 1 equivalent of epoxy group, the functional group of curing agent is the ratio of 0.5 ~ 1.5 equivalent, preferably 0.8 ~ 1.2 equivalent.This
Outside, cause the polymerization of epoxy group and the mixing ratio of cured curing agent is made to be, be 0.1 relative to 100 mass parts of epoxy resin
~ 10 mass parts, more preferably 0.2 ~ 5 mass parts.
Containing in flame-retardant epoxy resin omposition made of phosphorous epoxy resin (A) of the invention, as viscosity tune
It saves, organic solvent can also be used.It as workable organic solvent, does not provide particularly, can enumerate: N, N dimethyl
The alcohols such as the ketones such as the ethers such as the amides such as formamide, ethylene glycol single methyl ether, acetone, methyl ethyl ketone, methanol, ethyl alcohol, benzene,
Toluene etc. is aromatic hydrocarbon etc., can be with epoxy resin concentration by one of these solvents or a variety of solvents mixed
The range of 20 ~ 90 mass % is cooperated.
In the present composition, as needed, curing accelerator can be used.Example as workable curing accelerator
Son can be enumerated: the imidazoles such as 2 methylimidazoles, 2 ethyl imidazol(e)s, 2 ethyl, 4 methylimidazole, 2 (dimethylaminomethyls)
Tertiary amines, triphenylphosphine, tricyclohexyl phosphine, the triphenylphosphine triphens such as phenol, 1,8 diazabicyclos (5,4,0) endecatylene 7
The metallic compounds such as the phosphines such as base borine, tin octoate.Relative to the epoxy resin ingredient in composition epoxy resin of the invention
100 mass parts can according to need the curing accelerator using 0.02 ~ 5.0 mass parts.It, can be with by using curing accelerator
It reduces solidification temperature or shortens curing time.
Filler can be used in the present composition as needed.It is specific enumerable: aluminium hydroxide, magnesium hydroxide, talcum,
Calcination of talc, clay, kaolin, boehmite, titanium oxide, glass powder, silica air bag (シ リ カ バ ル ー Application) etc. are inorganic
Filler can also cooperate pigment etc..As the reasons why usually using inorganic filling material, raising impact resistance can be enumerated.In addition,
When using metal hydroxides such as aluminium hydroxide, magnesium hydroxides, work as flame retardant, it less can also be true even if phosphorus containing ratio
Environment friendly flame-retardant.Especially if use level is not 10 mass % or more, then the effect of impact resistance is small.But if use level is super
150 mass % are crossed, then are reduced as project necessary to laminated plate purposes, that is, cementability.In addition, may be used also in above-mentioned resin combination
To contain the cellulosics packing materials, particle rubber, thermoplastic elastic such as glass fibre, pulp fibers, synthetic fibers, ceramic fibre
The organic filler materials such as body.
By solidifying composition epoxy resin of the invention, available epoxy resin cured product.When solidification, such as can be with
By becoming the forms such as resin sheet, the copper foil of resin, prepreg, lamination is carried out and heat-pressure curing, so as to
To the phosphorous epoxy resin cured product as laminated plate.
Production has used the phosphorous composition epoxy resin of phosphorous epoxy resin (A) of the invention, heat solid
Change, whereby evaluate laminated plate phosphorous epoxy resin cured product as a result, by phosphorus compound, naphtoquinone compounds and have it is specific
Molecular weight distribution epoxy resin (a) reaction obtained by phosphorous epoxy resin (A), with by known phosphorus compound and
The phosphorous epoxy resin that epoxy resin obtains is compared, and only low viscosity, operability be not good, and can have both high heat resistance
Property and high adhesiveness, and then anti-flammability can also be improved.
Embodiment
Embodiment and comparative example are enumerated to specifically describe the present invention, but the present invention is not limited to these.Not special
In the case where explanation, " part " indicates that mass parts, " % " indicate quality %.Measuring method is respectively adopted the following method and is measured.
Measuring method is as follows.
Epoxide equivalent: according to JIS K7236.
Two nucleome containing ratios, three nucleome containing ratios, four nucleome containing ratios, the above containing ratio of five nucleomes, number-average molecular weight
(Mn), weight average molecular weight (Mw) and dispersion degree (Mw/Mn): molecular weight distribution is measured using gel permeation chromatography, two nucleomes contain
There are rate, three nucleome containing ratios, four nucleome containing ratios, the above containing ratio of five nucleomes to be calculated by the area % at peak, number-average molecular weight, again
Average molecular weight, dispersion degree by using standard monodisperse polystyrene (TOSOH Co., Ltd A 500, A 1000, A 2500,
A 5000, F 1, F 2, F 4, F 10, F 20, F 40) standard curve that finds out converts.Specifically, using in main body (east
Cao Co. Ltd. system HLC 8220GPC) on have in-linely column (TOSOH Co., Ltd TSKgelG4000HXL,
TSKgelG3000HXL, TSKgelG2000HXL) equipment, make 40 DEG C of column temperature.In addition, eluent uses tetrahydrofuran, stream
Speed is 1ml/min, and detector uses RI (differential refractometer) detector.
Phosphorus containing ratio: sulfuric acid, hydrochloric acid, perchloric acid are added in sample, is heated and is carried out wet combustion, make whole phosphorus
Atom becomes orthophosphoric acid.Make metavanadate and molybdic acid reactant salt in sulfuric acid solution, measures phosphovanadomolybdic acid network generated
The absorbance of object (リ Application バ ナ ー De モ リ Block デ Application acid wrong fount) at 420nm is closed, using preparatory made of potassium dihydrogen phosphate
Standard curve, the phosphorus atoms containing ratio found out are indicated with %.The phosphorus containing ratio of laminated plate is as the resin component relative to laminated plate
Containing ratio indicate.
Peel strength of copper foil and layers cementing power: being measured according to JIS C 6481, and layers cementing power is at the 7th layer and
It is avulsed between 8 layers to measure.
Flammability: according to UL94 (the safety certification specification of Underwriters Laboratories Inc.).For 5
Test film is tested, by the 1st time and the 2nd contact flame (connecing inflammation) (5 difference respectively twice in total 10 contact flame)
The flaming combustion duration afterwards is indicated total time with the second.
Glass transition temperature DSC: Differential Scanning Calorimetry measurement device (エ ス ア イ ア イ Na ノ テ Network ノ ロ is used
ジ ー Co. Ltd. system EXSTAR6000 DSC6200), it is measured with 10 DEG C/min of Elevated Temperature Conditions, with DSC at this time
The temperature of extrapolated value indicates.
Glass transition temperature TMA: thermo-mechanical analysis device (ー plants of ロ ジ of Network ノ of ノ テ of イ Na of イ ア of エ ス ア is used
Formula commercial firm EXSTAR6000 TMA/SS120U), it is measured with 5 DEG C/min of Elevated Temperature Conditions, with TMA extrapolation at this time
The temperature of value indicates.
Epoxy resin used in embodiment and comparative example is as follows.
エ Port ト ー ト YDPN 638 (the universal novolac type epoxy resin of Nippon Steel Chemical Co., Ltd's system, two nucleomes
22 area % of containing ratio, three nucleome containing ratios, 15 area %, three nucleomes and four nucleome containing ratios add up to 25 area %, five nucleomes
The above 53 area % of containing ratio, number-average molecular weight 528, weight average molecular weight 1127, dispersion degree 2.13, epoxide equivalent 176g/eq) (ginseng
According to Fig. 1)
170 (Nippon Steel Chemical Co., Ltd bisphenol f type epoxy resin epoxide equivalent 170g/ of エ ポ ト ー ト YDF
eq)。
Synthesis example 1 (synthesis of linear phenol-aldehyde resin)
Into 4 mouthfuls of glass system detachable flask for having agitating device, thermometer, condenser pipe, nitrogen gatherer
2500 parts of phenol, 7.5 parts of oxalic acid dihydrate is added, is stirred while importing nitrogen, carries out heat temperature raising.80
DEG C start that 474.1 parts of 37.4% formalin is added dropwise, spends the dropwise addition of completions in 30 minutes.And then reaction temperature is made to be maintained at 92 DEG C,
React within 3 hours.It heats up, reaction is generated into water on one side and is excluded to outside system, is warming up to 110 DEG C on one side.By residual benzene
Phenol is recycled under 160 DEG C, decompression, obtains linear phenol-aldehyde resin.And then temperature is increased, recycle a part of two nucleomes.It utilizes
Gel permeation chromatography measures the two nucleome containing ratios and three nucleome containing ratios of resulting linear phenol-aldehyde resin, respectively 10 faces
Product % and 38 area %.
Synthesis example 2 (synthesis of novolac type epoxy resin)
Into device same as synthesis example 1,665.8 parts of linear phenol-aldehyde resin, the epichlorohydrin of synthesis example 1 is added
2110.8 parts, 17 parts of water, are warming up to 50 DEG C while stirring.14.2 parts of 49% sodium hydrate aqueous solution is added, it is small to carry out 3
Shi Fanying.64 DEG C are warming up to, to cause the degree of reflux of water to be depressurized, spends 3 hours 49% sodium hydrate aqueous solutions of dropwise addition
It 457.7 parts, is reacted.70 DEG C are raised the temperature to, is dehydrated, makes 135 DEG C of temperature, recycles remaining epichlorohydrin.It is extensive
Again to normal pressure, being added 1232 parts of MIBK makes to dissolve.1200 parts of ion exchange water are added, stirring is stood, and by-product salt is dissolved
In water and remove.It is subsequently added into 37.4 parts of 49% sodium hydrate aqueous solution, is stirred to react at 80 DEG C 90 minutes, purify anti-
It answers.Additional MIBK, is washed for several times, removes ionic impurity.Recycling design obtains phenol aldehyde type epoxy resin.Two nucleomes contain
Have 9 area % of rate, three nucleome containing ratios, 36 area %, three nucleomes and four nucleome containing ratios adds up to 53 area %, more than five nucleomes
38 area % of containing ratio, number-average molecular weight 513, weight average molecular weight 713, dispersion degree 1.39, epoxide equivalent 174g/eq are (referring to figure
2)。
Embodiment 1
Into device same as synthesis example 1, HCA (9,10 dihydro of Sanko Co., Ltd.'s system, 9 oxa-, 10 phosphorus is added
Miscellaneous luxuriant and rich with fragrance 10 oxide phosphorus containing ratio 14.2%) 127 parts, 270 parts of toluene, it is dissolved by heating.Then heat release one is paid attention on one side
Side be added 70 parts of Isosorbide-5-Nitrae naphthoquinones (98% or more Tokyo Chemical Industry Co., Ltd's purity), keep the temperature at 90 DEG C hereinafter,
It is kept for 30 minutes.And then temperature is slowly increased, it is kept for 2 hours at a reflux temperature.After recycling a part of toluene, synthesis is added
804 parts of the novolac type epoxy resin of example 2, is stirred while importing nitrogen, is warming up to 130 DEG C.By triphenylphosphine
0.20 part is added as catalyst, carries out reacting for 3 hours at 160 DEG C.The epoxide equivalent of resulting epoxy resin is 276g/
Eq, phosphorus containing ratio are 1.8%.As a result it is summarized in table 1.
Embodiment 2
141 parts of HCA, 77 parts of 1,4 naphthoquinones, synthesis example 2 782 parts of novolac type epoxy resin, triphenylphosphine
It 0.22 part, is similarly operated with embodiment 1 in addition to this.The epoxide equivalent of resulting epoxy resin is 294g/eq, phosphorus contains
Having rate is 2.0%.As a result it is summarized in table 1.
Embodiment 3
155 parts of HCA, 85 parts of 1,4 naphthoquinones, synthesis example 2 760 parts of novolac type epoxy resin, triphenylphosphine
It 0.24 part, is similarly operated with embodiment 1 in addition to this.The epoxide equivalent of resulting epoxy resin is 317g/eq, phosphorus contains
Having rate is 2.2%.As a result it is summarized in table 1.
Embodiment 4
141 parts of HCA, 83 parts of 1,4 naphthoquinones, synthesis example 2 726 parts of novolac type epoxy resin, triphenylphosphine
0.22 part, and then cooperate 50 parts of YDF 170B simultaneously with novolac type epoxy resin, carried out in addition to this with embodiment 1 together
The operation of sample.The epoxide equivalent of resulting epoxy resin is 297g/eq, phosphorus containing ratio is 2.0%.As a result it is summarized in table 1.
Embodiment 5
155 parts of HCA, 57 parts of 1,4 naphthoquinones, synthesis example 2 638 parts of novolac type epoxy resin, triphenylphosphine
0.21 part, and then cooperate 170 150 parts of YDF simultaneously with novolac type epoxy resin, carried out in addition to this with embodiment 1 together
The operation of sample.The epoxide equivalent of resulting epoxy resin is 286g/eq, phosphorus containing ratio is 2.2%.As a result it is summarized in table 1.
Embodiment 6
155 parts of HCA, 34 parts of 1,4 naphthoquinones, synthesis example 2 777 parts of novolac type epoxy resin, triphenylphosphine
0.19 part, and then cooperate (the Showa Denko K. K line style phenolic aldehyde tree of BRG 555 simultaneously with novolac type epoxy resin
Rouge) 34 parts, similarly operated with embodiment 1 in addition to this.The epoxide equivalent of resulting epoxy resin is 310g/eq, phosphorus
Containing ratio is 2.2%.As a result it is summarized in table 1.
Embodiment 7
155 parts of HCA, 23 parts of 1,4 naphthoquinones, synthesis example 2 779 parts of novolac type epoxy resin, triphenylphosphine
0.18 part, and then cooperate 555 43 parts of BRG simultaneously with novolac type epoxy resin, carried out in addition to this with embodiment 1 equally
Operation.The epoxide equivalent of resulting epoxy resin is 310g/eq, phosphorus containing ratio is 2.2%.As a result it is summarized in table 1.
[table 1]
。
Comparative example 1
638 824 parts of YDPN, 176 parts of HCA are added into device same as synthesis example 1. while importing nitrogen
It is stirred, carries out heat temperature raising.0.18 part is added using triphenylphosphine as catalyst at 130 DEG C, 3 are carried out at 160 DEG C
Hour reaction.The epoxide equivalent of resulting epoxy resin is 263g/eq, phosphorus containing ratio is 2.5%.As a result it is summarized in table 1.
Comparative example 2
176 parts of 824 parts of novolac type epoxy resin, the HCA of synthesis example 2 are carried out with comparative example 1 equally in addition to this
Operation.The epoxide equivalent of resulting epoxy resin is 266g/eq, phosphorus containing ratio is 2.5%.As a result it is summarized in table 1.
Comparative example 3
141 parts of HCA, 77 parts of Isosorbide-5-Nitrae naphthoquinones, 638 782 parts of YDPN, 0.22 part of triphenylphosphine, in addition to this with implementation
Example 1 is similarly operated.The epoxide equivalent of resulting epoxy resin is 303g/eq, phosphorus containing ratio is 2.0%.As a result it is summarized in
Table 1.
Comparative example 4
155 parts of HCA, 80 parts of 1,4 naphthoquinones, 638 465 parts of YDPN, 0.23 part of triphenylphosphine, and then with line style phenolic aldehyde
Type epoxy resin cooperates 170 300 parts of YDF simultaneously, is similarly operated with embodiment 1 in addition to this.Resulting asphalt mixtures modified by epoxy resin
The epoxide equivalent of rouge is 311g/eq, phosphorus containing ratio is 2.2%.As a result it is summarized in table 1.
8 ~ embodiment of embodiment 14 and 5 ~ comparative example of comparative example 8
By 1 ~ embodiment of embodiment 7,1 ~ comparative example of comparative example 4 epoxy resin, as curing agent dicyandiamide according to table 2
Prescription cooperation, be dissolved in methyl ethyl ketone, propylene glycol monomethyl ether, N, the mixed solvent of N dimethylformamide modulation
In, obtain composition epoxy resin varnish.
Resulting resin composition Chinese varnish is soaked in glass cloth WEA 7628 XS13 (Nitto Boseki Co. Ltd's system
0.18mm is thick) in.Glass cloth through being impregnated with is dried with 150 DEG C of recirculation furnace, obtains prepreg.It will be resulting pre-
8 overlappings of leaching material, it is lower on it to be overlapped copper foil (Mitsu Mining & Smelting Co., Ltd 3EC), carry out 130 DEG C × 15 minutes and
The heating of 170 DEG C × 20Kg/cm2 × 70 minute, pressurization, obtain laminated plate.The vitrifying of laminated plate measured by TMA, DSC, DMS
Transition temperature, peel strength of copper foil, layers cementing power, the result of flame retardant test are summarized in table 2.
[table 2]
。
As shown in table 1, table 2, by the phosphorus compound of general formula (1) expression, naphtoquinone compounds and there is specific molecular weight distribution
Epoxy resin (a) reaction obtained from phosphorous epoxy resin (A), and use the asphalt mixtures modified by epoxy resin not reacted naphtoquinone compounds
Rouge, novolac type epoxy resin without specific molecular weight distribution situation compare, be low viscosity and glass transition
Temperature, bonding force are high, and obtain anti-flammability with low phosphorus containing ratio.
Industrial availability
The present invention is by specific phosphorus compound, naphtoquinone compounds and epoxy resin (a) with specific molecular weight distribution
Phosphorous epoxy resin (A) obtained from being reacted as essential component, it is excellent to may be used as anti-flammability, heat resistance, cementability
The epoxy resin of different circuit board use.
Claims (6)
1. phosphorous composition epoxy resin, wherein using phosphorous epoxy resin (A) and curing agent as essential component, to have
Solvent, curing accelerator and filler are formed as any ingredient,
Wherein, above-mentioned phosphorous epoxy resin (A) is phosphorus compound, naphtoquinone compounds and the epoxy resin (a) for indicating general formula (1)
Phosphorous epoxy resin obtained from being reacted as essential component, wherein epoxy resin (a) is in gel permeation chromatography
Measurement in, have two nucleome containing ratios be 15 area % or less, three nucleome containing ratios are 15 area of area % ~ 60 %, three nucleomes and
Total containing ratio of four nucleomes is 30 area of area % ~ 70 %, containing ratios more than five nucleomes is 45 area % hereinafter, number-average molecular weight
For the novolac type epoxy resin of 350 ~ 600 molecular weight distribution；
Gel permeation chromatography determination condition:
Using having TOSOH Co., Ltd TSKgelG4000HXL, TSKgelG3000HXL, TSKgelG2000HXL in-linely
Equipment, make 40 DEG C of column temperature；Eluent uses tetrahydrofuran, flow velocity 1ml/min, and detector uses RI (differential refractometer)
Detector；Measuring sample is the THF that sample 0.1g is dissolved in 10ml；Two nucleome containing ratios and three are calculated using resulting chromatography
Nucleome containing ratio utilizes the standard curve determination number-average molecular weight of standard polystyren；
R1 and R2 indicates alkyl in formula, can be the same or different, R1, R2 can be formed together cyclic structure, n with phosphorus atoms
Indicate 0 or 1.
2. phosphorous composition epoxy resin described in claim 1, wherein the epoxy relative to phosphorous epoxy resin (A)
1 equivalent of base cooperates 0.3 equivalent of active group ~ 1.5 equivalents of curing agent to form.
3. epoxy resin cured product is to form phosphorous epoxy resin composition of any of claims 1 or 2.
4. prepreg is to be impregnated with phosphorous composition epoxy resin of any of claims 1 or 2 to form in the substrate.
5. laminated plate is to form phosphorous epoxy resin composition of any of claims 1 or 2.
6. circuit substrate is to form phosphorous epoxy resin composition of any of claims 1 or 2.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810193561.6A CN108314774B (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing the epoxy resin as essential component, and cured product |
| CN201811147674.9A CN109293881B (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing the epoxy resin as essential component, and cured product |
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|---|---|---|---|
| JP2012135707 | 2012-06-15 | ||
| JP2012-135707 | 2012-06-15 | ||
| PCT/JP2013/063865 WO2013187184A1 (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing phosphorus-containing epoxy resin as essential component, and cured product |
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| CN201811147674.9A Division CN109293881B (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing the epoxy resin as essential component, and cured product |
| CN201810193561.6A Division CN108314774B (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing the epoxy resin as essential component, and cured product |
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| CN201811147674.9A Active CN109293881B (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing the epoxy resin as essential component, and cured product |
| CN201810193561.6A Active CN108314774B (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing the epoxy resin as essential component, and cured product |
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| CN201810193561.6A Active CN108314774B (en) | 2012-06-15 | 2013-05-13 | Phosphorus-containing epoxy resin, composition containing the epoxy resin as essential component, and cured product |
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| KR (1) | KR102038173B1 (en) |
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| JP6670045B2 (en) * | 2015-03-13 | 2020-03-18 | 日鉄ケミカル＆マテリアル株式会社 | Oxazolidone ring-containing epoxy resin, production method thereof, epoxy resin composition and cured product |
| JP6770793B2 (en) * | 2015-08-19 | 2020-10-21 | 日鉄ケミカル＆マテリアル株式会社 | Flame-retardant epoxy resin composition and its cured product |
| CN110114385B (en) * | 2016-12-27 | 2022-03-01 | 日铁化学材料株式会社 | Curable epoxy resin composition and fiber-reinforced composite material using same |
| JP2019104821A (en) * | 2017-12-12 | 2019-06-27 | 日鉄ケミカル＆マテリアル株式会社 | Epoxy resin composition and cured product of the same |
| KR20210047861A (en) * | 2018-08-27 | 2021-04-30 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | Phosphorus-containing epoxy resin, epoxy resin composition, prepreg, laminate, circuit board material and cured product |
| JP7211744B2 (en) * | 2018-09-19 | 2023-01-24 | 日鉄ケミカル＆マテリアル株式会社 | Epoxy resin composition and cured product thereof |
| JP7211829B2 (en) * | 2019-01-23 | 2023-01-24 | 日鉄ケミカル＆マテリアル株式会社 | Epoxy resin composition and cured product thereof |
| JP2020122034A (en) * | 2019-01-29 | 2020-08-13 | 日鉄ケミカル＆マテリアル株式会社 | Epoxy resin composition, and cured product of the same |
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| JP3092009B2 (en) | 1990-05-01 | 2000-09-25 | 東都化成株式会社 | Flame retardant and thermosetting flame-retardant resin composition containing the flame retardant |
| JP3268498B2 (en) | 1990-05-01 | 2002-03-25 | 東都化成株式会社 | Phosphorus-containing flame-retardant epoxy resin |
| JP2823057B2 (en) * | 1990-12-20 | 1998-11-11 | 日本化薬株式会社 | Manufacturing method of epoxy resin |
| JP3613724B2 (en) | 1997-09-09 | 2005-01-26 | 東都化成株式会社 | Phosphorus-containing epoxy resin composition |
| JP3533973B2 (en) | 1998-01-27 | 2004-06-07 | 東都化成株式会社 | Phosphorus-containing epoxy resin composition |
| JP2001123049A (en) | 1999-10-28 | 2001-05-08 | Dainippon Ink & Chem Inc | Flame-retardant epoxy resin composition |
| JP3651843B2 (en) * | 1999-12-16 | 2005-05-25 | 住友ベークライト株式会社 | Method for producing phenolic resin |
| JP4588834B2 (en) | 2000-04-06 | 2010-12-01 | パナソニック電工株式会社 | Phosphorus-containing epoxy resin composition, flame-retardant resin sheet using the phosphorus-containing epoxy resin, metal foil with resin, prepreg and laminate, multilayer board |
| JP2002012739A (en) * | 2000-06-29 | 2002-01-15 | Nippon Kayaku Co Ltd | Flame-retardant epoxy resin composition and use thereof |
| JP4837175B2 (en) * | 2001-02-23 | 2011-12-14 | 新日鐵化学株式会社 | Phosphorus-containing epoxy resin composition |
| JP4906020B2 (en) | 2001-07-26 | 2012-03-28 | 新日鐵化学株式会社 | Phosphorus-containing phenol resin and epoxy resin composition using the phenol resin |
| JP4435791B2 (en) * | 2001-11-16 | 2010-03-24 | 旭有機材工業株式会社 | Method for producing novolac-type phenolic resin and resin-coated sand |
| CN100560631C (en) * | 2004-06-29 | 2009-11-18 | 旭化成电子材料株式会社 | Fire retarded epoxy resin composition |
| KR100840065B1 (en) * | 2004-07-13 | 2008-06-19 | 히다치 가세고교 가부시끼가이샤 | Epoxy resin molding material for sealing and electronic component device |
| WO2009060987A1 (en) * | 2007-11-09 | 2009-05-14 | Tohto Kasei Co., Ltd. | Phosphorus-containing epoxy resin and phosphorus-containing epoxy resin composition, process for producing the same, and curable resin composition and cured object each containing or obtained from the resin and the resin composition |
| JP5547386B2 (en) * | 2008-09-25 | 2014-07-09 | パナソニック株式会社 | Epoxy resin composition for prepreg, prepreg, and multilayer printed wiring board |
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| JP5686512B2 (en) * | 2009-11-05 | 2015-03-18 | 新日鉄住金化学株式会社 | Phosphorus-containing epoxy resin, resin composition, and flame-retardant cured product thereof |
| JP5544184B2 (en) * | 2010-02-08 | 2014-07-09 | 新日鉄住金化学株式会社 | Method for producing phosphorus-containing epoxy resin, epoxy resin composition and cured product thereof |
| JP5579008B2 (en) * | 2010-09-29 | 2014-08-27 | 新日鉄住金化学株式会社 | Phosphorus-containing epoxy resin |
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| Publication number | Publication date |
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| CN109293881B (en) | 2021-04-13 |
| JPWO2013187184A1 (en) | 2016-02-04 |
| KR20150031237A (en) | 2015-03-23 |
| JP6067699B2 (en) | 2017-01-25 |
| CN109293881A (en) | 2019-02-01 |
| CN104379626A (en) | 2015-02-25 |
| SG11201408343TA (en) | 2015-01-29 |
| KR102038173B1 (en) | 2019-10-29 |
| CN108314774A (en) | 2018-07-24 |
| TWI598371B (en) | 2017-09-11 |
| TW201402632A (en) | 2014-01-16 |
| WO2013187184A1 (en) | 2013-12-19 |
| CN108314774B (en) | 2021-02-12 |
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