JP2011144387A - 熱硬化性樹脂組成物およびその硬化物 - Google Patents
熱硬化性樹脂組成物およびその硬化物 Download PDFInfo
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- JP2011144387A JP2011144387A JP2011064260A JP2011064260A JP2011144387A JP 2011144387 A JP2011144387 A JP 2011144387A JP 2011064260 A JP2011064260 A JP 2011064260A JP 2011064260 A JP2011064260 A JP 2011064260A JP 2011144387 A JP2011144387 A JP 2011144387A
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- Prior art keywords
- polyimide resin
- general formula
- resin
- resin composition
- thermosetting
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 96
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 79
- 229920001721 polyimide Polymers 0.000 claims abstract description 217
- 239000009719 polyimide resin Substances 0.000 claims abstract description 208
- -1 nitrogen-containing compound Chemical class 0.000 claims abstract description 73
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 229920005989 resin Polymers 0.000 claims description 57
- 239000011347 resin Substances 0.000 claims description 57
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 33
- 150000003949 imides Chemical class 0.000 claims description 31
- 150000001639 boron compounds Chemical class 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 150000004693 imidazolium salts Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 27
- 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 26
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 9
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- 125000004018 acid anhydride group Chemical group 0.000 description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 8
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000004642 Polyimide Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
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- 229910052802 copper Inorganic materials 0.000 description 6
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
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- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 229910003470 tongbaite Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical compound C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 150000005219 trimethyl ethers Chemical class 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 description 1
- FYAMVEZOQXNCIE-UHFFFAOYSA-N tris(3-methylphenyl) borate Chemical compound CC1=CC=CC(OB(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 FYAMVEZOQXNCIE-UHFFFAOYSA-N 0.000 description 1
- ROEKPHSQKWBJKS-UHFFFAOYSA-N tris(4-methylphenyl) borate Chemical compound C1=CC(C)=CC=C1OB(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 ROEKPHSQKWBJKS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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- 230000004580 weight loss Effects 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
製法1:ポリイソシアネート化合物と酸無水物基を有する化合物とを用いて直接イミド化する方法(イソシアネート法)。
製法2:酸無水物基を有する化合物とジアミン化合物とを反応させ、アミック酸を合成した後に、このアミック酸の脱水反応を行いイミド閉環させる方法。
等が挙げられる。
また、前記一般式(a4−4)で表される構造を有するポリイミド樹脂は、例えば、前記アミック酸法において、ベンゾフェノンテトラカルボン酸無水物とアルキル置換のビフェニルジアミンとを反応させ、アミド化及びイミド化すれば良い。また、前記イソシアネート法においては、無水トリメリット酸とアルキル置換のビフェニルジイソシアネートとのイミド化により得ることができる。
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、GBL(ガンマブチロラクトン)1422.8gとMDI(ジフェニルメタンジイソシアネート)250g(1.0モル)とTMA(無水トリメリット酸)134.3(0.7モル)とTMA−H(シクロヘキサン−1,3,4−トリカルボン酸−3,4−無水物)59.4g(0.3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160℃まで昇温した後、この温度で5時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は茶色の透明液体となった。25℃での粘度が10Pa・sの樹脂固形分20%で溶液酸価が1.8(KOHmg/g)のポリイミド樹脂(A−1)の溶液(ポリイミド樹脂がγーブチロラクトンに溶解した樹脂組成物)を得た。尚、樹脂の酸価は1.8(KOHmg/g)であった。また、ゲルパーミエーションクロマトグラフィー(GPC)の測定の結果、重量平均分子量64000であった。
上記構造中nのセグメントは0.843mmol/g、mのセグメントは1.967mmol/gであった。
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、GBL 1446.3gとMDI 240g(0.96モル)とTMA 134.3(0.7モル)とTMA−H 39.6g(0.2モル)及びBTDA(ベンゾフェノンテトラカルボン酸無水物)32.2g(0.1モル)とを仕込み、攪拌を行いながら発熱に注意して2時間かけて170℃まで昇温した後、この温度で5時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は茶色の透明液体となった。25℃での粘度が8Pa・sの樹脂固形分20%で溶液酸価が2.48(KOHmg/g)のポリイミド樹脂(A−2)の溶液(ポリイミド樹脂がγーブチロラクトンに溶解した樹脂組成物)を得た。尚、樹脂の酸価は2.48(KOHmg/g)であった。また、GPC測定により重量平均分子量は52000であった。
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、GBL 1451.2gとMDI 125g(0.5モル)とDMBPDI(4,4´−ジイソシアネート−3,3´−ジメチル−1,1´−ビフェニル)132g(0.5モル)とTMA 134.4(0.7モル)とTMA−H 59.4g(0.3モル)とを仕込み、攪拌を行いながら発熱に注意して2時間かけて160℃まで昇温した後、この温度で5時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は茶色の透明液体となった。25℃での粘度を測定た結果、6Pa.s(25℃)で樹脂固形分は17%であった。これをポリイミド樹脂(A−3)の溶液(ポリイミド樹脂がγーブチロラクトンに溶解した樹脂組成物)と略記する。尚、樹脂溶液酸価〔3.2(KOHmg/g)〕より平均分子量は5960と結論される。
a1:0.965mmol/g
a2:0.413mmol/g
a3:0.965mmol/g
a4:0.413mmol/g
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、GBL 1386.56gとTDI(2,4−トリレンジイソシアネート) 52.2g(0.3モル)とDMBPDI(4,4´−ジイソシアネート−3,3´−ジメチル−1,1´−ビフェニル)184.8g(0.7モル)とTMA 138.24(0.72モル)とTMA−H 59.4g(0.3モル)とを仕込み、攪拌を行いながら発熱に注意して2時間かけて160℃まで昇温した後、この温度で5時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は茶色の透明液体となった。25℃での粘度を測定た結果、8Pa.s(25℃)で樹脂固形分は17%であった。これをポリイミド樹脂(A−4)の溶液(ポリイミド樹脂がγーブチロラクトンに溶解した樹脂組成物)と略記する。尚、樹脂溶液酸価〔2.9(KOHmg/g)〕より平均分子量は6577と結論される。
a1:0.623mmol/g
a2:0.260mmol/g
a3:1.453mmol/g
a4:0.606mmol/g
攪拌装置、温度計、コンデンサーを付けたフラスコに、EDGA(エチルジグリコールアセテート) 4951gと、イソホロ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(イソシアネート基含有率18.2%、イソシアヌレート環含有トリイソシアネート含有率85%)2760g(イソシアネート基として12モル)と、ポリテールHA〔三菱化学(株)製の両末端に水酸基を有する水素添加液状ポリブタジエン、数平均分子量2,100、水酸基価51.2mgKOH/g〕2191g(水酸基として2モル)とを仕込み、攪拌を行いながら発熱に注意して80℃に昇温した。この温度で3時間ウレタン化反応を行った。次いで、さらにEDGA1536gとTMA 1536g(8モル)を仕込み、160℃まで昇温し4時間反応させて薄茶色のポリイミド樹脂(A−5)の溶液(ポリイミド樹脂がEDGAに溶解した樹脂組成物)を得た。樹脂固形分は48.2%であった。尚、樹脂溶液酸価〔38.1(KOHmg/g)〕であり、GPCより数平均分子量は5,900、重量平均分子量は24,000であった。
第1表に示す配合にて本発明の熱硬化性樹脂組成物1を調製した。尚、組成物の調整においては室温にて配合、攪拌して調整を行った。得られた熱硬化性樹脂組成物1の溶剤溶解性、経時溶解性、塗装作業性、耐熱性、難燃性、機械物性及び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。
保存安定性試験は調製直後の熱硬化型樹脂組成物1の溶剤溶解性及び長期間静置後の溶剤溶解性を評価する事により行った。調製直後の熱硬化型組成物を蓋付ガラス瓶に25ml入れ、その外観を観察し、以下の評価基準にて評価した。これを調製直後の熱硬化型樹脂組成物1の溶剤溶解性とした。その後、熱硬化型樹脂組成物1が入った蓋付ガラス瓶を25℃で7日間静置した後、熱硬化型樹脂組成物1の外観を観察し、経時溶剤溶解性として以下の評価基準にて評価した。
△ :流動性があるが濁りが発生する。
× :透明感が無い、流動性がない、分離している、のいずれか1つ以上に該当
熱硬化型樹脂組成物をブリキ板に0.152ミルのアプリケーターで室温にて塗装した。塗装外観について以下の評価基準で評価した。尚、以下の実施例及び比較例において調製した樹脂溶液に固形分が混じっている時は樹脂溶液の温度を120℃まで上げて固形分を一度溶解させてから塗装した。
△:不透明であるがフラットな面である。
×:不透明で表面がフラットな面ではない。
熱硬化型樹脂組成物を硬化後の膜厚が30μmになるように銅泊がラミネートされたガラスエポキシ基板上に塗装し、200℃の乾燥機で60分間乾燥した後、室温まで冷却し試験片を作成した。この試験片を260℃の溶融ハンダ浴に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。また、耐熱性は後述するTgを測定する事でも評価した。Tgが高いほど耐熱性に優れる。
△:塗膜にフクレ、はがれ等異常が若干見られる。
×:塗膜全面にフクレ、はがれ等異常が見られる。
熱分解測定を行うことにより評価した。
<試験片の作製>
熱硬化型樹脂組成物1を得られる塗膜の膜厚が30μm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50℃の乾燥機で30分間、100℃の乾燥機で30分間、200℃の乾燥機で60分間乾燥して塗膜(フィルム)を作成した。室温まで冷却した後、塗膜(フィルム)を基板から単離して測定用試料とした。
示差熱‐熱重量同時測定(TG−DGA)により熱分解測定を行った。具体的には、エスアイアイナノテクノロジー株式会社製TG/DTA6200にて500℃における熱重量減少率を測定した。測定は試料を測定用アルミ製容器(70μl)に内包できる大きさに切り出し、初期試料質量は、5.5から5.8mgの間に調整を行った。室温から500℃まで10℃/分の昇温速度で窒素気流下加熱し測定を行った。評価は、質量の減量%で行い、その値が小さい程、耐熱性が良好であることを示す。
機械物性は塗膜(フィルム)の引張試験を行い、弾性率と破断強度と破断伸度を求めることにより評価した。
<試験片の作製>
熱硬化型樹脂組成物を得られる塗膜の膜厚が30μm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50℃の乾燥機で30分間、100℃の乾燥機で30分間、200℃の乾燥機で60分間乾燥して塗膜(フィルム)を作成した。室温まで冷却した後、塗膜(フィルム)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、弾性率と破断強度と破断伸度を求めた。弾性率の値が低いほど柔軟性に優れる塗膜であることを表す。破断伸度の値が高いほど柔軟性に優れる塗膜であることを表す。そして、破断強度の値が高いほど強靭な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
<試験用試験片の作製>
熱硬化型樹脂組成物を硬化後の膜厚が30μm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。さらに線膨張係数に使用した温度域は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。
<試験用試験片の作製>
熱硬化型樹脂組成物を硬化後の膜厚が30μm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10mm、長さ40mmに切り出し、このフィルムを長手方向に半分に折り曲げ測定用試料とした。
折り曲げたフィルム試料の方端をクランプでつかんで水平に固定して別の方端にライターでゆっくり炎を近づけ着火し、以下の基準で評価を行った。
○:フィルム試料に着火するがすぐ消える。
△:フィルム試料に着火するがクランプの手前で消える。
×:フィルム試料がクランプまで燃え尽きる。
第1表から第3表に示す配合にて調製した以外は実施例1と同様にして熱硬化性樹脂組成物4、7、10及び比較対照用熱硬化性樹脂組成物1´〜5´を得た。実施例1と同様の評価を行い、その結果を第4表〜第6表に示す。
TPP:トリフェニルフォスフィン
Claims (14)
- 前記一般式(b3)で表されるホウ素化合物のZ+がイミダゾリウム塩である請求項1記載の熱硬化性樹脂組成物。
- 前記ホウ素化合物(B)の含有量がポリイミド樹脂100質量部に対して0.5〜30質量部である請求項1記載の熱硬化性樹脂組成物。
- 前記ポリイミド樹脂(A)が環状脂肪族炭化水素構造を有するポリイミド樹脂である請求項1から4のいずれか1項記載の熱硬化性樹脂組成物。
- 前記環状脂肪族炭化水素構造を有するポリイミド樹脂が環状脂肪族炭化水素構造に直結したイミド5員環構造を有するポリイミド樹脂である請求項5記載の熱硬化性樹脂組成物。
- 前記一般式(a2)で表される構造を有するポリイミド樹脂が一般式(a2)で表される構造を、ポリイミド樹脂の固形分質量を基準として0.02〜2.0mmol/gの濃度で含有するポリイミド樹脂である請求項7記載の熱硬化性樹脂組成物。
- 前記一般式(a1−5)、一般式(a1−7)、一般式(a1−8)、一般式(a2−7)及び一般式(a2−8)で示される構造中のR4がメチル基である請求項4または8記載の熱硬化性樹脂組成物。
- 前記ポリイミド樹脂(A)の末端基が、カルボン酸および/またはカルボン酸の無水物であり、固形分酸価が1〜50である請求項1から12のいずれか1項記載の熱硬化性樹脂組成物。
- 前記ポリイミド樹脂がガンマブチロラクトンに25℃で10質量%となるように溶解したときに、ガンマブチロラクトンに可溶であるポリイミド樹脂である請求項12記載の熱硬化性樹脂組成物。
- 請求項1〜13のいずれか1項記載の熱硬化性樹脂組成物を硬化してなることを特徴とする硬化物。
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KR20120038392A (ko) | 2012-04-23 |
CN102449069B (zh) | 2014-02-12 |
JP4807602B2 (ja) | 2011-11-02 |
WO2010137548A1 (ja) | 2010-12-02 |
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