JP2020090651A - ポリフェニレンエーテル、硬化性組成物、ドライフィルム、硬化物、および電子部品 - Google Patents
ポリフェニレンエーテル、硬化性組成物、ドライフィルム、硬化物、および電子部品 Download PDFInfo
- Publication number
- JP2020090651A JP2020090651A JP2019132316A JP2019132316A JP2020090651A JP 2020090651 A JP2020090651 A JP 2020090651A JP 2019132316 A JP2019132316 A JP 2019132316A JP 2019132316 A JP2019132316 A JP 2019132316A JP 2020090651 A JP2020090651 A JP 2020090651A
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- JP
- Japan
- Prior art keywords
- polyphenylene ether
- phenols
- side chain
- unsaturated carbon
- curable composition
- 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.)
- Granted
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- 229920001955 polyphenylene ether Polymers 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 53
- 150000002989 phenols Chemical class 0.000 claims abstract description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 239000002994 raw material Substances 0.000 claims abstract description 25
- 125000000524 functional group Chemical group 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 23
- 238000004132 cross linking Methods 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 8
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 238000001723 curing Methods 0.000 description 36
- -1 polyphenylene Polymers 0.000 description 26
- 239000002904 solvent Substances 0.000 description 24
- 150000002430 hydrocarbons Chemical group 0.000 description 20
- 229920001971 elastomer Polymers 0.000 description 19
- 239000000806 elastomer Substances 0.000 description 17
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 150000002978 peroxides Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000013329 compounding Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000004891 communication Methods 0.000 description 5
- 239000011889 copper foil Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WREVCRYZAWNLRZ-UHFFFAOYSA-N 2-allyl-6-methyl-phenol Chemical compound CC1=CC=CC(CC=C)=C1O WREVCRYZAWNLRZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000034628 Celiac artery compression syndrome Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000000569 multi-angle light scattering Methods 0.000 description 3
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-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
- 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-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
- CIRRFAQIWQFQSS-UHFFFAOYSA-N 6-ethyl-o-cresol Chemical compound CCC1=CC=CC(C)=C1O CIRRFAQIWQFQSS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
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- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
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- 150000002440 hydroxy compounds Chemical class 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
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- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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Abstract
Description
前記側鎖不飽和炭素結合を有するポリフェニレンエーテルが、少なくとも下記条件1および下記条件2をいずれも満たすフェノール類(A)、または、少なくとも下記条件1を満たし下記条件2を満たさないフェノール類(B)と下記条件1を満たさず下記条件2を満たすフェノール類(C)の混合物を含む原料フェノール類からなることを特徴とする側鎖エポキシ化ポリフェニレンエーテルである。
(条件1)
オルト位およびパラ位に水素原子を有する
(条件2)
パラ位に水素原子を有し、不飽和炭素結合を含む官能基を有する
前記側鎖不飽和炭素結合を有するポリフェニレンエーテルが、少なくとも下記条件1および下記条件2をいずれも満たすフェノール類(A)、または、少なくとも下記条件1を満たし下記条件2を満たさないフェノール類(B)と下記条件1を満たさず下記条件2を満たすフェノール類(C)の混合物を含む原料フェノール類からなり、コンフォメーションプロットで算出された傾きが0.6未満であることを特徴とする側鎖エポキシ化ポリフェニレンエーテルである。
(条件1)
オルト位およびパラ位に水素原子を有する
(条件2)
パラ位に水素原子を有し、不飽和炭素結合を含む官能基を有する
本発明の側鎖エポキシ化ポリフェニレンエーテルは、分岐構造を有し、かつ、側鎖不飽和炭素結合を有する所定のポリフェニレンエーテルの側鎖不飽和炭素結合の一部または全部をエポキシ化したものである。側鎖不飽和炭素結合は、典型的には、ポリフェニレンエーテルの構成単位である原料フェノール類が置換基として有する不飽和炭素結合に由来する。
(条件1)
オルト位およびパラ位に水素原子を有する
(条件2)
パラ位に水素原子を有し、不飽和炭素結合を含む官能基を有する
ポリフェニレンエーテルのクロロホルム溶液を、0.1、0.15、0.2、0.25mg/mLの間隔で調製後、0.5mL/minで送液しながら屈折率差と濃度のグラフを作成し、傾きから屈折率増分dn/dcを計算する。次に、下記装置運転条件にて、絶対分子量を測定する。RI検出器のクロマトグラムとMALS検出器のクロマトグラムを参考に、分子量と回転半径の対数グラフ(コンフォメーションプロット)から、最小二乗法による回帰直線を求め、その傾きを算出する。
装置名 :HLC8320GPC
移動相 :クロロホルム
カラム :TOSOH TSKguardcolumnHHR−H
+TSKgelGMHHR−H(2本)
+TSKgelG2500HHR
流速 :0.6mL/min.
検出器 :DAWN HELEOS(MALS検出器)
+Optilab rEX(RI検出器、波長254nm)
試料濃度 :0.5mg/mL
試料溶媒 :移動相と同じ。試料5mgを移動相10mLで溶解
注入量 :200μL
フィルター :0.45μm
STD試薬 :標準ポリスチレン Mw 37,900
STD濃度 :1.5mg/mL
STD溶媒 :移動相と同じ。試料15mgを移動相10mLで溶解
分析時間 :100min
本発明の側鎖エポキシ化ポリフェニレンエーテルは、低誘電特性、耐溶剤性がより優れた硬化物が得られ、熱硬化温度を低下させることが可能なことから、様々な用途に適用することができる。
本発明の硬化性組成物は、上述した側鎖エポキシ化ポリフェニレンエーテルを含む。また、以下に説明する成分を含んでもよい。
硬化物は、上述した硬化性組成物を硬化することで得られる。
本発明のドライフィルムまたはプリプレグは、上述した硬化性組成物を基材に塗布して得られるものである。
本発明においては、上述のプリプレグを用いて積層板を作製することができる。
このような硬化物は、優れた誘電特性や耐熱性を有するため、電子部品用等に使用可能である。
側鎖エポキシ化PPEおよび非側鎖エポキシ化PPEを以下の通りに調製した。PPE−1〜PPE−4の合成に使用したフェノール類およびその配合比(モル比)、エポキシ化に関する情報を表1に示す。
(PPE−1に係る合成物の合成)
3Lの二つ口ナスフラスコに、ジ−μ−ヒドロキソ−ビス[(N,N,N’,N’−テトラメチルエチレンジアミン)銅(II)]クロリド(Cu/TMEDA)5.3gと、テトラメチルエチレンジアミン(TMEDA)5.7mLを加えて十分に溶解させ、10ml/minにて酸素を供給した。о−クレゾール10.0g、2−アリル−6−メチルフェノール13.7g、2,6−ジメチルフェノール90.3gをトルエン1.5Lに溶解させ、フラスコに滴下し、600rpmの回転速度で攪拌しながら40℃で6時間反応させた。反応終了後、メタノール20L:濃塩酸22mLの混合液で再沈殿させてろ過にて取り出し、80℃で24時間乾燥させ、PPE−1に係る合成物を得た。
滴下漏斗を備えた二つ口ナスフラスコに50gのPPE−1に係る合成物とテトラヒドロフラン400mLを加え、氷浴中で攪拌した。メタクロロ過安息香酸(mCPBA)31gをテトラヒドロフラン1.6Lに溶解させた溶液を30分かけて滴下し、室温で24時間攪拌した。反応溶液をメタノール中に再沈させて濾過により取り出し、80℃で24時間乾燥させてPPE−1を得た。
原料フェノール類の配合比を変更し、mCPBAを93g使用した以外は側鎖エポキシ化PPE−1の合成方法と同じ方法で側鎖エポキシ化PPE(PPE−2)を得た。
原料フェノール類の配合比を変更し、mCPBAを155g使用した以外は側鎖エポキシ化PPE−1の合成方法と同じ方法で側鎖エポキシ化PPE(PPE−3)を得た。
PPE−1に係る合成物(エポキシ化されていないポリフェニレンエーテル)をPPE−4とした。
各成分を以下の表に記載の質量配合割合で、固形分濃度が50質量%となるように、シクロヘキサノンを添加し、混合させワニスを作製した。
厚さ18μm銅箔のシャイン面に、各組成物を、硬化物の厚みが50μmになるようにアプリケーターで塗布した。次に、熱風式循環式乾燥炉で90℃30分乾燥させた。その後、熱風循環式乾燥炉で所定温度にて60分加熱し、硬化膜を得た。
具体的には、180℃の加熱で得た硬化膜が溶解しないものを「◎」、200℃の加熱で得た硬化膜が溶解しないものを「〇」、200℃の加熱で得た硬化膜が溶解したものを「×」と評価した。
誘電特性である比誘電率Dkおよび誘電正接Dfは、以下の方法に従って測定した。
厚さ18μm銅箔のシャイン面に、各組成物を、硬化物の厚みが50μmになるようにアプリケーターで塗布した。次に、熱風式循環式乾燥炉で90℃30分乾燥させた。その後、熱風循環式乾燥炉で180℃60分加熱した。組成物を硬化後、銅箔をエッチング除去して硬化膜を得た。
硬化膜を長さ80mm、幅45mm、厚み50μmに切断し、これを試験片としてSPDR(Split Post Dielectric Resonator)共振器法により測定した。測定器には、キーサイトテクノロジー合同会社製のベクトル型ネットワークアナライザE5071C、SPDR共振器、計算プログラムはQWED社製のものを用いた。条件は、周波数10GHz、測定温度25℃とした。
Claims (6)
- 側鎖不飽和炭素結合を有するポリフェニレンエーテルの側鎖不飽和炭素結合の一部または全部をエポキシ化して得られる側鎖エポキシ化ポリフェニレンエーテルであって、
前記側鎖不飽和炭素結合を有するポリフェニレンエーテルが、少なくとも下記条件1および下記条件2をいずれも満たすフェノール類(A)、または、少なくとも下記条件1を満たし下記条件2を満たさないフェノール類(B)と下記条件1を満たさず下記条件2を満たすフェノール類(C)の混合物を含む原料フェノール類からなることを特徴とする側鎖エポキシ化ポリフェニレンエーテル。
(条件1)
オルト位およびパラ位に水素原子を有する
(条件2)
パラ位に水素原子を有し、不飽和炭素結合を含む官能基を有する - 請求項1に記載の側鎖エポキシ化ポリフェニレンエーテルと、エポキシ基反応性架橋型硬化剤と、を含む硬化性組成物。
- 請求項2に記載の硬化性組成物を基材に塗布して得られる、ドライフィルムまたはプリプレグ。
- 請求項2に記載の硬化性組成物を硬化して得られる、硬化物。
- 請求項4に記載の硬化物を含む、積層板。
- 請求項4に記載の硬化物を有する、電子部品。
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JPH0476018A (ja) * | 1990-07-18 | 1992-03-10 | Asahi Chem Ind Co Ltd | 新規な硬化性ポリフェニレンエーテル・エポキシ樹脂組成物 |
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JP2008115280A (ja) * | 2006-11-06 | 2008-05-22 | Hitachi Ltd | 低誘電損失樹脂組成物、その硬化物およびそれを用いた電子部品 |
JP2009067894A (ja) * | 2007-09-13 | 2009-04-02 | Hitachi Ltd | 樹脂組成物および電子部品 |
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JPS5827719A (ja) * | 1981-08-11 | 1983-02-18 | Mitsubishi Chem Ind Ltd | 側鎖にアリル基を有するポリフエニレンエ−テル |
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