JP2008239868A - 熱硬化性ポリイミド樹脂組成物 - Google Patents
熱硬化性ポリイミド樹脂組成物 Download PDFInfo
- Publication number
- JP2008239868A JP2008239868A JP2007084446A JP2007084446A JP2008239868A JP 2008239868 A JP2008239868 A JP 2008239868A JP 2007084446 A JP2007084446 A JP 2007084446A JP 2007084446 A JP2007084446 A JP 2007084446A JP 2008239868 A JP2008239868 A JP 2008239868A
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- JP
- Japan
- Prior art keywords
- group
- general formula
- polyimide resin
- resin composition
- epoxy resin
- 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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- 229920001721 polyimide Polymers 0.000 title claims abstract description 188
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 185
- 239000000203 mixture Substances 0.000 title claims abstract description 101
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 92
- -1 glycidyloxy group Chemical group 0.000 claims abstract description 203
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 143
- 239000003822 epoxy resin Substances 0.000 claims abstract description 136
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 136
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 13
- 150000002989 phenols Chemical class 0.000 claims abstract description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- 238000006467 substitution reaction Methods 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 97
- 229920005862 polyol Polymers 0.000 claims description 73
- 150000003077 polyols Chemical class 0.000 claims description 44
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 40
- 125000001624 naphthyl group Chemical group 0.000 claims description 33
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 31
- 125000004018 acid anhydride group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 230000001476 alcoholic effect Effects 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 229920000098 polyolefin Polymers 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 229920000515 polycarbonate Polymers 0.000 claims description 11
- 239000004417 polycarbonate Substances 0.000 claims description 11
- 125000006267 biphenyl group Chemical group 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229920001296 polysiloxane Polymers 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 7
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 5
- 238000003860 storage Methods 0.000 abstract description 9
- 230000000704 physical effect Effects 0.000 abstract description 5
- 238000000034 method Methods 0.000 description 99
- 238000006243 chemical reaction Methods 0.000 description 75
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- 229920006287 phenoxy resin Polymers 0.000 description 65
- 239000013034 phenoxy resin Substances 0.000 description 65
- 230000001588 bifunctional effect Effects 0.000 description 60
- 239000005056 polyisocyanate Substances 0.000 description 59
- 229920001228 polyisocyanate Polymers 0.000 description 59
- 150000008065 acid anhydrides Chemical class 0.000 description 57
- 239000010408 film Substances 0.000 description 56
- 239000011248 coating agent Substances 0.000 description 45
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 36
- 239000010410 layer Substances 0.000 description 35
- 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 32
- 239000002904 solvent Substances 0.000 description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 26
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 26
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 25
- 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 25
- 238000001723 curing Methods 0.000 description 25
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 22
- 239000004305 biphenyl Substances 0.000 description 19
- 235000010290 biphenyl Nutrition 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 18
- 229920003986 novolac Polymers 0.000 description 18
- 239000011342 resin composition Substances 0.000 description 18
- 238000011156 evaluation Methods 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000004020 conductor Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 239000011889 copper foil Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 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 10
- 239000012948 isocyanate Substances 0.000 description 10
- 150000007524 organic acids Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000002313 adhesive film Substances 0.000 description 9
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 229930003836 cresol Natural products 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 0 C*NC(O*O)=O Chemical compound C*NC(O*O)=O 0.000 description 7
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- 125000001931 aliphatic group Chemical group 0.000 description 7
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
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- 238000012360 testing method Methods 0.000 description 7
- 125000005591 trimellitate group Chemical group 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 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 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
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- 238000010030 laminating Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
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- 239000005062 Polybutadiene Substances 0.000 description 5
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
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Landscapes
- Epoxy Resins (AREA)
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Abstract
Description
(1)フェノール系化合物の構造残基と、フェノール性水酸基およびイソシアネート基の反応にて生成されるウレタン結合とを有するポリイミド樹脂と、芳香族炭化水素における芳香環上の隣接する2箇所の置換位置において、炭素原子又は酸素原子を介して2つの前記芳香族炭化水素が結合した芳香族多環骨格を有し、かつ、該芳香族多環骨格上の置換基としてグリシジルオキシ基を有するエポキシ樹脂とを含有する樹脂組成物の硬化物は、耐熱性、電気特性、柔軟性に優れる。
本発明は上記の知見を基に完成したものである。
測定装置 ; 東ソー株式会社製 HLC−8220GPC
カラム ; 東ソー株式会社製ガードカラムSUPER HZ−H
+東ソー株式会社製 TSKgel SUPER HZm−mを4本
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 GPC−8020
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/min
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.2重量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100ml)
1.エピハロヒドリンと2官能フェノールとをアルカリ存在下で反応させて製造する方法(以下、第1法と略記する)。
2.2官能エポキシ樹脂と2官能フェノールとを触媒存在下で反応させて製造する方法(以下、第2法と略記する)。
4.2官能エポキシ樹脂と2官能フェノールとを反応させる際に、2官能エポキシ樹脂と2官能フェノールのうち少なくとも一方がビスフェノールS骨格を有するような化合物を用いる条件にて反応させる方法(以下、第2−1法と略記する)。
5.エピハロヒドリンとナフタレン骨格を有する2官能フェノールとをアルカリ存在下で反応させて製造する方法(以下、第1−2法と略記する)。
6.2官能エポキシ樹脂と2官能フェノールとを反応させる際に、2官能エポキシ樹脂と2官能フェノールのうち少なくとも一方がナフタレン骨格を有するような化合物を用いる条件にて反応させる方法(以下、第2−2法と略記する)。
7.エピハロヒドリンとビスフェノールS骨格を含有する2官能フェノールとナフタレン骨格を含有する2官能フェノールとをアルカリ存在下で反応させて製造する方法(以下、第1−3法と略記する)。
8.2官能エポキシ樹脂と2官能フェノールとを反応させる際に、得られるフェノキシ樹脂がビスフェノールS骨格及びナフタレン骨格とを含有するように2官能エポキシ樹脂と2官能フェノールとを選択使用する(以下、第2−3法と略記する)。
10.2官能エポキシ樹脂と2官能フェノールとを反応させる際に、得られるフェノキシ樹脂がビスフェノールS骨格及びビフェニル骨格とを含有するように2官能エポキシ樹脂と2官能フェノールとを選択使用する(以下、第2−4法と略記する)。
12.2官能エポキシ樹脂と2官能フェノールとを反応させる際に、得られるフェノキシ樹脂がビフェニル骨格及びナフタレン骨格とを含有するように2官能エポキシ樹脂と2官能フェノールとを選択使用する方法(以下、第2−5法と略記する)。
13.エピハロヒドリンとビスフェノールSとナフタレン骨格を有する2官能フェノールとビフェニル骨格を有する2官能フェノールとをアルカリ存在下で反応させて製造する方法(以下、第1−6法と略記する)。
14.2官能エポキシ樹脂と2官能フェノールとを反応させる際に、得られるフェノキシ樹脂がビスフェノールS骨格、ナフタレン骨格及びビフェニル骨格とを含有するように2官能エポキシ樹脂と2官能フェノールとを選択使用する方法(以下、第2−6法と略記する)。
攪拌装置、温度計およびコンデンサーを付けたフラスコに、DMAC(ジメチルアセトアミド)140gと、TMEG(エチレングリコールビスアンヒドロトリメリテート)98.4g(0.24モル)と、BPS(ビスフェノールS)40g(0.16モル)と、MDI(ジフェニルメタンジイソシアネート)40g(0.16モル)と、HDI(ヘキサメチレンジイソシアネート)26.9g(0.16モル)とを仕込み、攪拌を行いながら発熱に注意して80℃に昇温し、この温度で1時間かけて溶解、反応させ、更に2時間かけて120℃まで昇温した後、この温度で1時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は茶色の液体となった。DMACにて樹脂固形分濃度を55%に調整し、25℃での粘度が100Pa・sのポリイミド樹脂(A−1)の溶液を得た。
攪拌装置、温度計およびコンデンサーを付けたフラスコに、DMAC 156.8gと、TMEG 65.6g(0.16モル)と、BP(ビフェノール)29.8g(0.16モル)と、MDI 40g(0.16モル)と、1,6−ヘキサンジイソシアネートから誘導されるイソシアヌレート環を有するポリイソシアネート(以下、HDI−Nと略記する。イソシアネート基含有率23.5%、イソシアヌレート環含有トリイソシアネート含有率63.3%)21.4g(イソシアネート基として0.12モル)とを仕込み、攪拌を行いながら発熱に注意して100℃に昇温し、この温度で7時間反応させた。反応は発泡とともに進行し、系内はクリアな茶色の液体となった。25℃での粘度が15Pa・sのポリイミド樹脂(A−2)の溶液を得た。
攪拌装置、温度計およびコンデンサーを付けたフラスコに、γ−ブチロラクトン203.5gと、TMEG(エチレングリコールビスアンヒドロトリメリテート)57.4g(0.14モル)と、BPF(ビスフェノールF)28.28g(0.14モル)と、TDI(トルエンジイソシアネート)48.72g(0.28モル)と、HGMPD−C(1,6−ヘキサンジオールとメチルペンタンジオールから得られるポリカーボネートジオール:水酸基当量=113.7KOH−mg/g)69.08g(水酸基量として0.14モル)とを仕込み、攪拌を行いながら発熱に注意して80℃に昇温し、この温度で1時間かけて溶解、反応させ、更に2時間かけて120℃まで昇温した後、この温度で4時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は黒茶色の液体となった。25℃での粘度が15Pa・sのポリイミド樹脂(A−3)の溶液(樹脂分48.4%)を得た。
撹拌装置と加熱装置が付いた1リットル四つ口フラスコに、トリメチルハイドロキノン152g(1.0モル)をトルエン500gとエチレングリコールモノエチルエーテル200gの混合溶媒に溶解した。その溶液にパラトルエンスルホン酸4.6gを加え、41%ホルマリン44g(0.6モル)を発熱に注意しながら滴下して、水分を留去しながら100〜120℃で15時間撹拌した。次いで、冷却して析出結晶を濾別し、中性になるまで繰り返し水で洗浄した後に、乾燥して下記の多価ヒドロキシ化合物、132g〔ゲルパーミエーションクロマトグラフィー(GPC)による純度:98%)を得た。尚、構造は、NMRスペクトル(13C)とIRスペクトル(KBr)とマススペクトルから同定した。
2,7ジヒドロキシナフタレン320g(2.0モル)及びホルマリンをビフェニルアルデヒド236g(1.2モル)に変更した以外は合成例4と同様にして、目的の下記構造式で表わされる多価フェノール化合物276g(GPC純度:99%)を得た。この化合物の水酸基当量は157g/eq.(アセチル化法)であり、GPCによる純度は99%であった。
第1表に示す配合にて本発明の熱硬化性ポリポリイミド樹脂組成物1を調製した。得られた熱硬化性ポリイミド樹脂組成物1の硬化塗膜の電気特性、耐熱性、寸法安定性、難燃性、相溶性、塗膜増膜性、機械物性及び熱硬化性ポリイミド樹脂組成物1の寸法安定性を下記方法に従って評価した。その結果を第3表に示す。
電気特性は塗膜の誘電率(ε)と誘電損失(Tanδ)とを測定することにより評価した。熱硬化性樹ポリイミド脂組成物1を硬化後の膜厚が80μmになるようにブリキ基板上に塗装し、70℃の乾燥機で20分間乾燥した後、200℃で1時間硬化させ冷却した後、剥離した硬化塗膜を切り出した測定用試料を、アジレントテクノロジー社製4291Bを用いて、周波数は100MHzの条件で、測定雰囲気の温度は23度の条件で誘電率(ε)と誘電損失(Tanδ)とを測定した。
耐熱性の評価は硬化塗膜のガラス転移点(Tg)の測定とハンダ浴浸漬法により行った。寸法安定性の評価は線膨張係数を測定することにより行った。
<試験用試験片の作製>
熱硬化性ポリウレタン樹脂組成物1を硬化後の膜厚が50μmになるようにブリキ基板上に塗装し、70℃の乾燥機で20分間乾燥した後、200℃で1時間硬化させ冷却した後、剥離した硬化塗膜を幅5mm、長さ30mmに切り出し、測定用試料とした。
セイコー電子(株)製熱分析システムTMA−SS6000を用いて、試料長10mm、昇温速度10℃/分、荷重30mNの条件でTMA(Thermal Mechanical Analysis)法により測定した。なお、Tgは、TMA測定での温度−寸法変化曲線からその変極点を求め、その温度をTgとした。Tgが高いほど耐熱性に優れることを表す。線膨張係数は温度域50〜60℃、及び110〜120℃での試料長の変位より求めた。線膨張係数が小さいほど寸法安定性に優れることを示す。
尚、第3表、第4表において温度域50〜60℃における線膨張係数の測定結果を「線膨張係数1」と、温度域110〜120℃における線膨張係数の測定結果を「線膨張係数2」と略記する。線膨張係数の単位はPPM(cm/cm/℃)×106である。
<試験片の作成>
熱硬化性ポリウレタン樹脂組成物を硬化後の膜厚が50μmになるように銅箔がラミネートされたガラスエポキシ基板上に塗装し、70℃の乾燥機で30分間乾燥した後、170℃で1時間硬化させた後、室温まで冷却し、硬化塗膜を作成した。
硬化塗膜を260℃のハンダ浴に30秒浸漬し、室温に冷却した。このハンダ浴の浸漬操作を合計3回行い、硬化塗膜の外観について以下の評価基準で評価した。
○:塗膜に外観以上は見られない。
△:塗膜にフクレ、はがれ等以上が若干見られる。
×:塗膜全体にフクレ、はがれ等異常が見られる。
ブリキ板に熱硬化性ポリウレタン樹脂組成物1を乾燥膜圧を80μmになるように塗装し、70℃の乾燥機で20分間乾燥させた後、200℃で1時間硬化させた。室温まで冷却した後に硬化塗膜を10×100mmの短冊状に切り、ブリキ板から剥離してテストピースとした。このテストピースをブンゼンバーナーの炎にて着火させ、炎から静かに離し、テストピースの着火炎が消えるかどうかの試験を行った。この操作を3回行い、下記の基準に従って評価した。尚、テストピースは長手方向に垂直にクランプに固定し、上部に火をつけ、評価を行った。
○:3回中すべて火が消えた。
△:3回中1〜2回火が消えた。
×:3回中3回燃え尽きた。
熱硬化性ポリイミド樹脂組成物1を密栓したガラスビンに保存し、40℃で1週間後の状態を観察した。目視にて下記基準に従って評価した。
○:凝集物、沈殿物がなく、且つ、高粘度化せずに流動性があるもの。
△:凝集物、沈殿物がなないもののテーリングまたは高粘度化が起こったもの。
×:ゲル化がおこったもの。
熱硬化性ポリイミド樹脂組成物を調製した際の相溶状態と、調製後の熱硬化性ポリイミド樹脂組成物1をガラス板に塗装し、120℃で乾燥した後の塗膜の状態を、下記の評価基準で評価した。
評価基準
○:熱硬化性ポリイミド樹脂組成物の調製において攪拌により均一となり、塗膜面にも異物等が見られない。
△:熱硬化性ポリイミド樹脂組成物の調製において攪拌により均一になりにくく、塗膜面にもやや異物等が見られる。
×:熱硬化性ポリイミド樹脂組成物の調製において均一に溶解せず、塗膜面は、はじき、異物、不溶解物が確認できる。
熱硬化性ポリイミド樹脂組成物10を乾燥後の膜厚が30μmになるようにブリキ板にアプリケーターにて塗布後、110℃で30分間乾燥させて得た試験片を、室温にて24時間放置し、塗膜外観を以下の評価基準で評価した。
評価基準
○:塗膜にクラック等の異常は見られない。
△:塗膜に若干クラックが見られる。
×:塗膜全面にクラックが発生した。
機械物性は塗膜の引張試験を行うことにより評価した。
<試験片の作製>
熱硬化性樹脂ポリイミド組成物を硬化後の膜厚が50μmになるようにブリキ基板上に塗装した。次いで、この塗装板を70℃の乾燥機で20分間乾燥した後、200℃で1時間硬化させて硬化塗膜を作成した。室温まで冷却した後、硬化塗膜を所定の大きさに切り出し、基板から単離して測定用試料とした。
測定用試料を5枚作成し、下記の条件で引張試験を行い、破断強度と破断伸度を求めた。破断強度と破断伸度の値が高いほど機械物性に優れる塗膜であることを表す。
測定機器:東洋ボールドウィン社製テンシロン
サンプル形状:10mm×70mm
チャック間:20mm
引張速度:10mm/min
測定雰囲気:22℃、45%RH
第1表、第2表に示す配合で配合した以外は実施例1と同様にして熱硬化ポリイミド性樹脂組成物2〜12及び比較対照用熱硬化性樹脂組成物1´〜5´を調製した。これを用いて実施例1と同様に各種評価を行い、その結果を第5表〜第8表に示す。
N680:クレゾールノボラック型エポキシ樹脂、エポキシ当量214 軟化点81℃
EP2050:固形ビスフェノールA型エポキシ樹脂、エポキシ当量640
DBTL:ジブチルチンジラウレート
2E4MZ:2−エチル−4−メチル−イミダゾール
DBTA:ジブチルチンアセテート
CNR:オルソクレゾールノボラック型樹脂 融点 90℃ 水酸基当量=105
BPF:ビスフェノールF
Claims (19)
- 前記一般式(13)で表される構造が、該構造中のYとして数平均分子量が300〜5,000であるポリオール化合物から2つの水酸基を除いた残基を有する構造である請求項7記載の熱硬化性ポリイミド樹脂組成物。
- 前記一般式(13)で表される構造が、該構造中のYとしてガラス転移温度が−150〜0℃である残基を有する構造である請求項7記載の熱硬化性ポリイミド樹脂組成物。
- 前記一般式(13)中のYが1分子中に少なくとも2個のアルコール性水酸基を有するポリオレフィンポリオールから2つの水酸基を除いた残基、1分子中に少なくとも2個のアルコール性水酸基を有するポリエーテルポリオールから2つの水酸基を除いた残基、1分子中に少なくとも2個のアルコール性水酸基を有するポリカーボネートポリオールから2つの水酸基を除いた残基、1分子中に少なくとも2個のアルコール性水酸基を有するポリエステルポリオールから2つの水酸基を除いた残基および1分子中に少なくとも2個のアルコール性水酸基を有するポリシロキサンポリオールから2つの水酸基を除いた残基からなる群から選ばれる1種以上の残基である請求項7記載の熱硬化性ポリイミド樹脂組成物。
- 前記エポキシ樹脂(B)が、該エポキシ樹脂の構造中に存在する前記芳香族多環骨格にメチル基を有するものである請求項1記載の熱硬化性ポリイミド樹脂組成物。
- 前記エポキシ樹脂(B)中の芳香族炭化水素がナフタレンである請求項1記載の熱硬化性ポリイミド樹脂組成物。
- 前記エポキシ樹脂(B)が、エポキシ当量240〜330g/eqのエポキシ樹脂である請求項1の熱硬化性ポリイミド樹脂組成物。
- 前記エポキシ樹脂(B)が該エポキシ樹脂(B)中の芳香族炭素原子数に対する前記芳香族多環構造部を構成する炭素原子数の割合が20%以上のエポキシ樹脂である請求項1記載の熱硬化性ポリイミド樹脂組成物。
- 硬化触媒を含有する請求項1〜16のいずれか1項記載の熱硬化性ポリイミド樹脂組成物。
- 更に、ウレタン化触媒を含有する請求項1〜16のいずれか1項記載の熱硬化性ポリイミド樹脂組成物。
- 請求項1〜18いずれか1項記載の熱硬化性ポリイミド樹脂組成物を熱硬化してなることを特徴とする硬化物。
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