JP2007009124A - Antistatic epoxy resin composition and molded article - Google Patents
Antistatic epoxy resin composition and molded article Download PDFInfo
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- JP2007009124A JP2007009124A JP2005194502A JP2005194502A JP2007009124A JP 2007009124 A JP2007009124 A JP 2007009124A JP 2005194502 A JP2005194502 A JP 2005194502A JP 2005194502 A JP2005194502 A JP 2005194502A JP 2007009124 A JP2007009124 A JP 2007009124A
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 62
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 61
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 239000004844 aliphatic epoxy resin Substances 0.000 claims abstract description 16
- 239000002608 ionic liquid Substances 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 238000010894 electron beam technology Methods 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 abstract description 6
- 229920005989 resin Polymers 0.000 abstract description 6
- 239000011347 resin Substances 0.000 abstract description 6
- 238000005299 abrasion Methods 0.000 abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000002216 antistatic agent Substances 0.000 description 11
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 10
- -1 alkali metal salt Chemical class 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 5
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 4
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 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 4
- 238000000034 method Methods 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 238000012663 cationic photopolymerization Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 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 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- HYYJOCXNESGFSB-UHFFFAOYSA-N 1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CNCC1CO1 HYYJOCXNESGFSB-UHFFFAOYSA-N 0.000 description 1
- JSZMNEHRJUWKCF-UHFFFAOYSA-N 2-(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)acetic acid Chemical compound C1C(CC(O)=O)C(C)CC2OC21 JSZMNEHRJUWKCF-UHFFFAOYSA-N 0.000 description 1
- SUTCVRHWHOUKJP-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetic acid Chemical compound C1C(CC(=O)O)CCC2OC21 SUTCVRHWHOUKJP-UHFFFAOYSA-N 0.000 description 1
- WKJICCKTDQDONB-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)OCC1OC1 WKJICCKTDQDONB-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VTPXYFSCMLIIFK-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propan-1-ol Chemical compound C1OC1COCC(COCC1OC1)(CO)COCC1CO1 VTPXYFSCMLIIFK-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- ZXOATMQSUNJNNG-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 ZXOATMQSUNJNNG-UHFFFAOYSA-N 0.000 description 1
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【課題】 優れた帯電防止能及び安定した帯電防止能を有し、かつ、耐摩耗性、機械的強度、及び透明性に優れたエポキシ樹脂成形体を与える帯電防止エポキシ樹脂組成物を提供。
【解決手段】 下式（１）で表されるイオン性液体がエポキシ樹脂原料に含有されてなることを特徴とする帯電防止エポキシ樹脂組成物。脂肪族系エポキシ樹脂１００質量部に対し、下式（１）のイオン性液体を０．０１〜２０質量部含有するか、また、芳香族系エポキシ樹脂５０〜８０質量部と、脂肪族系エポキシ樹脂２０〜５０質量部とからなるエポキシ樹脂組成物１００質量部に対し、下式（１）のイオン性液体を０．０１〜２０質量部含有する帯電防止エポキシ樹脂組成物が好ましい。
【化１】
（式中、Ｒは、それぞれ同一であっても異なっていてもよい炭素数１から２のアルキル基を表す。）
【選択図】 なし
PROBLEM TO BE SOLVED: To provide an antistatic epoxy resin composition which has an excellent antistatic ability and a stable antistatic ability, and gives an epoxy resin molded article excellent in abrasion resistance, mechanical strength and transparency.
An antistatic epoxy resin composition comprising an epoxy resin raw material containing an ionic liquid represented by the following formula (1). It contains 0.01 to 20 parts by mass of the ionic liquid of the following formula (1) with respect to 100 parts by mass of the aliphatic epoxy resin, or 50 to 80 parts by mass of the aromatic epoxy resin and the aliphatic epoxy. An antistatic epoxy resin composition containing 0.01 to 20 parts by mass of the ionic liquid of the following formula (1) with respect to 100 parts by mass of the epoxy resin composition comprising 20 to 50 parts by mass of the resin is preferable.
[Chemical 1]
(In the formula, R represents an alkyl group having 1 to 2 carbon atoms, which may be the same or different.)
[Selection figure] None
Description
本発明は、帯電防止エポキシ樹脂組成物及び成形体に関するものである。 The present invention relates to an antistatic epoxy resin composition and a molded body.
エポキシ樹脂は、優れた耐薬品性、耐磨耗性、接着性等の特徴を持つことから、塗料、建材などに使用され、また、電気絶縁性にも優れるため、電子部品の封止材や電子回路配線基板などにも広く使用されている。しかし、静電気を蓄積しやすいため帯電し、例えば、埃等の付着、あるいはスパークの発生等の問題を引き起こしやすい。 Epoxy resins are used in paints and building materials because they have excellent chemical resistance, wear resistance, adhesiveness, etc., and because they have excellent electrical insulation properties, Widely used in electronic circuit wiring boards. However, since it is easy to accumulate static electricity, it is charged and easily causes problems such as adhesion of dust, etc.
従来のエポキシ樹脂の帯電防止方法としては、導電性を有する金属粉や金属酸化物粉、カーボン繊維、カーボンブラックなどを未硬化のエポキシ樹脂組成物中に混練することによって導電性を付与させる方法が用いられてきたが、特にカーボンブラックなどを添加する方法では安定した帯電防止能は得られ難く、また外観も黒く着色したりしてしまう等の問題があった。 As a conventional antistatic method for epoxy resin, there is a method of imparting conductivity by kneading conductive metal powder or metal oxide powder, carbon fiber, carbon black, etc. in an uncured epoxy resin composition. Although it has been used, there has been a problem that a stable antistatic ability is difficult to obtain especially by a method of adding carbon black or the like, and the appearance is also colored black.
これらの問題に対し、特許文献１には、エポキシ樹脂組成物に、アルカリ金属塩とポリエーテル系高分子とを添加することで、安定した帯電防止能を与える組成物が開示されている。しかしながら該公報においては架橋構造をとらないポリエーテル系高分子を使用しているために、得られるエポキシ樹脂硬化物の機械的強度が不十分であるという問題があった。 With respect to these problems, Patent Document 1 discloses a composition that provides a stable antistatic ability by adding an alkali metal salt and a polyether polymer to an epoxy resin composition. However, in this publication, there is a problem that the obtained epoxy resin cured product has insufficient mechanical strength because it uses a polyether polymer that does not have a crosslinked structure.
特許文献２では、特許文献１の問題点を克服する為にポリエーテル系高分子の末端をグリシジル基としたポリアルキレングリコールジグリシジルエーテルを用い、これにアルカリ金属塩を添加してなるエポキシ樹脂組成物が開示されている。しかし、該組成物はアルカリ金属塩を溶解させているだけで有るために水に接触した後では帯電防止の性能が著しく損なわれると言った不具合があった。更に、エポキシ樹脂組成物に対して無機塩を加熱溶解させなければならないという煩雑な操作が必要であった。 In Patent Document 2, an epoxy resin composition obtained by using polyalkylene glycol diglycidyl ether having a glycidyl group at the end of a polyether polymer and adding an alkali metal salt thereto to overcome the problems of Patent Document 1 Things are disclosed. However, since the composition only has an alkali metal salt dissolved therein, there has been a problem that the antistatic performance is significantly impaired after contact with water. Furthermore, the complicated operation that the inorganic salt must be dissolved by heating in the epoxy resin composition is required.
また、特許文献３では、グリシジル基を持った第４級アンモニウム塩を含有させてなるエポキシ樹脂組成物及び、該樹脂組成物を紫外線、電子線などにより硬化させた帯電防止樹脂成形体が開示されている。該公報に、最も好ましい第４級アンモニウム塩として例示されているクロライド塩は耐熱性に劣るため、硬化時に過剰に熱がかかると成形体が黄変するといった問題や、該塩類が潮解しやすいため、組成物製造時においての取扱いが困難であるといった問題がある。 Patent Document 3 discloses an epoxy resin composition containing a quaternary ammonium salt having a glycidyl group, and an antistatic resin molded product obtained by curing the resin composition with ultraviolet rays, electron beams, or the like. ing. Since the chloride salt exemplified as the most preferable quaternary ammonium salt in the publication is inferior in heat resistance, the molded product is yellowed when excessively heated during curing, and the salts are easily deliquescent. There is a problem that it is difficult to handle at the time of producing the composition.
本発明は、優れた帯電防止能及び安定した帯電防止能を有し、かつ、耐摩耗性、機械的強度、及び透明性に優れたエポキシ樹脂成形体を与える帯電防止エポキシ樹脂組成物を提供することである。 The present invention provides an antistatic epoxy resin composition which has an excellent antistatic ability and a stable antistatic ability, and gives an epoxy resin molded article excellent in abrasion resistance, mechanical strength, and transparency. That is.
本発明者は、鋭意検討した結果、特定のイオン性液体がエポキシ樹脂原料に含有されてなるエポキシ樹脂組成物が、上記課題を解決する帯電防止エポキシ樹脂組成物及び成形体を与えることを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have found that an epoxy resin composition containing a specific ionic liquid in an epoxy resin raw material provides an antistatic epoxy resin composition and a molded product that solve the above-mentioned problems, The present invention has been completed.
すなわち本発明は、一般式（１）で表されるイオン性液体がエポキシ樹脂原料に含有されてなることを特徴とする帯電防止エポキシ樹脂組成物である。 That is, the present invention is an antistatic epoxy resin composition characterized in that an ionic liquid represented by the general formula (1) is contained in an epoxy resin raw material.
また、脂肪族系エポキシ樹脂１００質量部に対し、一般式（１）で表されるイオン性液体を０．０１〜２０質量部含有する事を特徴とする帯電防止エポキシ樹脂組成物である。 Moreover, it is an antistatic epoxy resin composition characterized by containing 0.01 to 20 parts by mass of the ionic liquid represented by the general formula (1) with respect to 100 parts by mass of the aliphatic epoxy resin.
また、芳香族系エポキシ樹脂５０〜８０質量部と、脂肪族系エポキシ樹脂２０〜５０質量部とからなるエポキシ樹脂組成物１００質量部に対し、一般式（１）で表されるイオン性液体を０．０１〜２０質量部含有する事を特徴とする帯電防止エポキシ樹脂組成物である。 Moreover, the ionic liquid represented by General formula (1) with respect to 100 mass parts of epoxy resin compositions which consist of 50-80 mass parts of aromatic epoxy resins and 20-50 mass parts of aliphatic epoxy resins. It is an antistatic epoxy resin composition characterized by containing 0.01-20 mass parts.
また、請求項１〜３のいずれか一項に記載の帯電防止エポキシ樹脂組成物を、硬化剤を用いて常温或いは加熱硬化させた事を特徴とする成形体である。 Moreover, it is the molded object characterized by having hardened the antistatic epoxy resin composition as described in any one of Claims 1-3 at normal temperature or heat-hardening using the hardening | curing agent.
また、請求項１又は２記載の帯電防止エポキシ樹脂組成物を、硬化剤に光カチオン重合開始剤を用いて紫外線又は電子線硬化させた事を特徴とする成形体である。 The molded article is characterized in that the antistatic epoxy resin composition according to claim 1 or 2 is cured with ultraviolet rays or electron beams using a cationic photopolymerization initiator as a curing agent.
本発明によれば、帯電防止剤として含有させる化合物として、エポキシ樹脂との相溶性も良く、エポキシ樹脂に架橋されるイオン性液体である第４級アンモニウム塩を用いる事により、エポキシ樹脂中への添加も容易であり、耐熱性に優れた帯電防止エポキシ樹脂組成物が得られる。また、耐摩耗性、機械的強度、透明性等、本来のエポキシ樹脂硬化物のもつ優れた特性を損なわず、帯電防止能の安定性、特に耐水性に優れた帯電防止エポキシ樹脂成形体を提供する事ができる。 According to the present invention, as a compound to be contained as an antistatic agent, compatibility with an epoxy resin is good, and by using a quaternary ammonium salt which is an ionic liquid crosslinked to the epoxy resin, Addition is easy and an antistatic epoxy resin composition excellent in heat resistance can be obtained. In addition, we provide antistatic epoxy resin moldings that have excellent antistatic performance, especially water resistance, without compromising the excellent properties of the original cured epoxy resin, such as wear resistance, mechanical strength, and transparency. I can do it.
以下、本発明を実施するための最良の形態について詳細に説明する。 Hereinafter, the best mode for carrying out the present invention will be described in detail.
本発明の帯電防止エポキシ樹脂組成物（以下、「本組成物」と略記する。）は、前記一般式（１）で示されるイオン性液体である第４級アンモニウム塩が、帯電防止剤としてエポキシ樹脂に含有されたものであり、該式中、Ｒは、それぞれ同一であっても異なっていてもよい炭素数１から２のアルキル基を表す。 In the antistatic epoxy resin composition of the present invention (hereinafter abbreviated as “the present composition”), a quaternary ammonium salt, which is an ionic liquid represented by the general formula (1), is used as an antistatic agent. In the formula, each R represents an alkyl group having 1 to 2 carbon atoms which may be the same or different.
前記一般式（１）で示される第４級アンモニウム塩は、例えば、特許第３２９８０２０号公報に記載の製造方法により得られる。すなわち、Ｎ位にグリシジル基を有する第４級アンモニウムクロライドを得、次いで、該化合物を、ビス（トリフルオロメタンスルホニル）イミドのリチウム塩またはナトリウム塩などのアルカリ金属塩と複分解させて、目的とする化合物を得ることができる。 The quaternary ammonium salt represented by the general formula (1) can be obtained, for example, by the production method described in Japanese Patent No. 3298020. That is, a quaternary ammonium chloride having a glycidyl group at the N-position is obtained, and then the compound is subjected to metathesis with an alkali metal salt such as a lithium salt or sodium salt of bis (trifluoromethanesulfonyl) imide to obtain a target compound. Can be obtained.
前記一般式（１）で示される第４級アンモニウム塩は、常温で液体を呈するイオン性液体であり、耐熱性に優れ、また、Ｎ位にグリシジル基を有することで、エポキシ樹脂との相溶性がよく、架橋可能で、エポキシ樹脂への添加も容易である。 The quaternary ammonium salt represented by the general formula (1) is an ionic liquid that exhibits a liquid at room temperature, has excellent heat resistance, and has a glycidyl group at the N position, thereby being compatible with an epoxy resin. It can be cross-linked and can be easily added to an epoxy resin.
本組成物は、前記帯電防止剤をエポキシ樹脂に含有させてなるものであり、該エポキシ樹脂としては、（Ａ）脂肪族系エポキシ樹脂、または、（Ｂ）脂肪族系エポキシ樹脂と芳香族系エポキシ樹脂との混合物からなるものが使用できる。 This composition contains the antistatic agent in an epoxy resin, and the epoxy resin includes (A) an aliphatic epoxy resin, or (B) an aliphatic epoxy resin and an aromatic resin. What consists of a mixture with an epoxy resin can be used.
以下に、本組成物の製造方法を説明する。 Below, the manufacturing method of this composition is demonstrated.
（Ａ）脂肪族系エポキシ樹脂を用いる場合には、該樹脂に所定量の前記帯電防止剤を添加させた後、撹拌・混合させて本組成物を得る。 When (A) an aliphatic epoxy resin is used, a predetermined amount of the antistatic agent is added to the resin, followed by stirring and mixing to obtain the present composition.
前記脂肪族系エポキシ樹脂の具体例としては、３，４−エポキシシクロヘキシルメチルカルボキシレート、３，４−エポキシ−６−メチルシクロヘキシルメチルカルボキシレート、ダイマー酸グリシジルエステル、ヘキサヒドロフタル酸グリシジルエステル、ジグリシジルエーテル、ブタンジオールジグリシジルエーテル、ヘキサヒドロビスフェノールＡジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、グリセリントリグリシジルエーテル、ペンタエリスリトールトリグリシジルエーテル、トリグリジシルイソシアヌレート、テトラグリシジル−１，３−ビスアミノメチルヘキサン、ジペンタエリスリトールヘキサグリシジルエーテル等が挙げられ、これらを単独で用いてもよいし、複数混合して用いても良い。また、脂肪族系エポキシモノマーのエポキシ当量の範囲は、１００〜１０００が好ましい。 Specific examples of the aliphatic epoxy resin include 3,4-epoxycyclohexylmethyl carboxylate, 3,4-epoxy-6-methylcyclohexylmethylcarboxylate, dimer acid glycidyl ester, hexahydrophthalic acid glycidyl ester, and diglycidyl. Ether, butanediol diglycidyl ether, hexahydrobisphenol A diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, glycerin triglycidyl ether, pentaerythritol tri Glycidyl ether, triglycidyl isocyanurate, tetraglycidyl-1,3-bisamino Chiruhekisan, dipentaerythritol hexa glycidyl ether and the like, may be used these alone, it may be used in multiple mixing. The epoxy equivalent range of the aliphatic epoxy monomer is preferably 100 to 1000.
本組成物に配合される帯電防止剤は、前記脂肪族系エポキシ樹脂１００質量部に対し、前記帯電防止剤を０．０１〜２０質量部となるよう含有させる事が好適である。配合量が０．０１質量部未満では、導電性が不十分となる場合があり、また、２０質量部超では、得られる成形体の機械的強度が低下する場合がある。 The antistatic agent blended in the present composition preferably contains 0.01 to 20 parts by mass of the antistatic agent with respect to 100 parts by mass of the aliphatic epoxy resin. If the blending amount is less than 0.01 parts by mass, the electrical conductivity may be insufficient, and if it exceeds 20 parts by mass, the mechanical strength of the resulting molded product may be reduced.
（Ｂ）脂肪族系エポキシ樹脂と芳香族系エポキシ樹脂との混合物を用いる場合には、該混合樹脂に所定量の前記帯電防止剤を添加させた後、撹拌・混合させて本発明の組成物を得る。 (B) In the case of using a mixture of an aliphatic epoxy resin and an aromatic epoxy resin, a predetermined amount of the antistatic agent is added to the mixed resin, followed by stirring and mixing. Get.
芳香族系エポキシ樹脂としては、１分子中に２個以上のグリジジル基を有し、かつ骨格にベンゼン環核を有するものである。例えば、ビスフェノール型のグリシジルエーテル、フェノールノボラック型のグリシジルエーテル、芳香族アミンのグリシジルアミン、芳香族カルボン酸のグリシジルエステル等が挙げられ、これら複数を混合して用いても良い。 The aromatic epoxy resin has two or more glycidyl groups in one molecule and a benzene ring nucleus in the skeleton. For example, bisphenol type glycidyl ether, phenol novolac type glycidyl ether, glycidyl amine of aromatic amine, glycidyl ester of aromatic carboxylic acid, and the like may be used in combination.
ビスフェノール型のグリシジルエーテルとしては、例えばビスフェノールＡジグリシジルエーテル、ビスフェノールＦジグリシジルエーテル、ビスフェノールＳジグリシジルエーテル、ビスフェノールＡＤジグリシジルエーテル、ブロム化ビスフェノールＡジグリシジルエーテル、テトラメチルビスフェノールＡジグリシジルエーテル、ビスフェノールのグリシジルエーテル等が挙げられる。 Examples of the bisphenol type glycidyl ether include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, bisphenol AD diglycidyl ether, brominated bisphenol A diglycidyl ether, tetramethylbisphenol A diglycidyl ether, and bisphenol. And glycidyl ether.
フェノールノボラック型のジグリシジルエーテルとしては、例えばフェノールノボラックのエポキシ樹脂、クレゾールノボラックのエポキシ樹脂等が挙げられる。 Examples of the phenol novolac-type diglycidyl ether include phenol novolac epoxy resins and cresol novolac epoxy resins.
芳香族アミンのジグリシジルアミンとしては、例えばテトラグリシジルジアミノジフェニルメタン、テトラグリシジルジメタキシレンジアミン、ジグリシジルアニリン、ジグリシジルトルイジン等が挙げられる。 Examples of the aromatic amine diglycidylamine include tetraglycidyldiaminodiphenylmethane, tetraglycidyldimetaxylenediamine, diglycidylaniline, and diglycidyltoluidine.
芳香族カルボン酸のグリシジルエステルとしては、例えばフタル酸ジグリシジルエステル、イソフタル酸ジグリシジルエステル、テレフタル酸ジグリシジルエステル等が挙げられる。 Examples of glycidyl esters of aromatic carboxylic acids include diglycidyl phthalate, diglycidyl isophthalate, and diglycidyl terephthalate.
また、本発明に使用される芳香族系エポキシ樹脂のエポキシ当量の範囲は１００〜４０００が好ましく、さらに好ましくは、１５０〜１０００である。 The range of the epoxy equivalent of the aromatic epoxy resin used in the present invention is preferably 100 to 4000, and more preferably 150 to 1000.
本組成物において配合される芳香族系エポキシ樹脂、脂肪族系エポキシ樹脂及び帯電防止剤は、芳香族系エポキシ樹脂５０〜８０質量部及び脂肪族系エポキシ樹脂２０〜５０質量部からなるエポキシ樹脂組成物１００質量部に対し、帯電防止剤を０．０１〜２０質量部となるよう配合させる事が好適である。
エポキシ樹脂組成物中、芳香族系エポキシ樹脂の配合量が５０質量部未満では、良好な機械的強度が得られにくく、また、８０質量部超では、帯電防止能が得られ難くなる。より好ましい範囲としては、５０〜７０質量部である。
また、前述の通り、耐電防止剤の配合量が０．０１質量部未満では、導電性が不十分となる場合があり、また、２０質量部超では、機械的強度が低下する場合がある。
The aromatic epoxy resin, aliphatic epoxy resin and antistatic agent blended in the present composition are epoxy resin compositions comprising 50-80 parts by mass of aromatic epoxy resin and 20-50 parts by mass of aliphatic epoxy resin. It is preferable to add the antistatic agent to 0.01 to 20 parts by mass with respect to 100 parts by mass of the product.
If the blending amount of the aromatic epoxy resin is less than 50 parts by mass in the epoxy resin composition, it is difficult to obtain good mechanical strength, and if it exceeds 80 parts by mass, it is difficult to obtain antistatic ability. A more preferable range is 50 to 70 parts by mass.
Further, as described above, when the blending amount of the antistatic agent is less than 0.01 parts by mass, the electrical conductivity may be insufficient, and when it exceeds 20 parts by mass, the mechanical strength may be decreased.
これら本組成物には、それぞれ必要に応じて、帯電防止能、耐摩耗性、機械的強度、及び透明性等の特性を損なわない程度に、着色顔料、フィラー、繊維、各種添加剤、溶剤、反応性希釈剤などを添加することも可能である。 In these compositions, if necessary, coloring pigments, fillers, fibers, various additives, solvents, to the extent that the properties such as antistatic ability, abrasion resistance, mechanical strength, and transparency are not impaired. It is also possible to add a reactive diluent or the like.
次いで、本発明の帯電防止エポキシ樹脂成形体（以下、「本成形体」と略記する。）について説明する。 Next, the antistatic epoxy resin molded product of the present invention (hereinafter abbreviated as “the molded product”) will be described.
本成形体は、前記説明した本組成物に硬化剤を添加し、常温或いは加熱温度下で硬化されたものである。ここで言う常温とは５℃から３０℃のことで、加熱温度下とは３０℃から１８０℃のことである。 The molded body is obtained by adding a curing agent to the above-described composition and curing at room temperature or heating temperature. The normal temperature mentioned here means 5 to 30 ° C., and the heating temperature means 30 to 180 ° C.
硬化剤としては、例えばポリメルカプタン、ポリアミド、脂肪族ポリアミン、脂環族ポリアミン、芳香族ポリアミン、酸無水物、フェノールノボラック、イミダゾール等が挙げられる。これら硬化剤の添加量は、エポキシ樹脂に対し、５から８０ｐｈｒ（parts per hundred parts of resin）であることが好ましい。 Examples of the curing agent include polymercaptan, polyamide, aliphatic polyamine, alicyclic polyamine, aromatic polyamine, acid anhydride, phenol novolac, and imidazole. The addition amount of these curing agents is preferably 5 to 80 phr (parts per hundred parts of resin) with respect to the epoxy resin.
また、本成形体は、前記説明した本組成物に光カチオン重合開始剤を添加し、紫外線又は電子線を照射することによって硬化されたものである。 Moreover, this molded object is hardened | cured by adding a photocationic polymerization initiator to this composition demonstrated above, and irradiating an ultraviolet-ray or an electron beam.
光カチオン重合開始剤としては、例えばジアゾニウム塩、スルホニウム塩、ヨードニウム塩等が挙げられ。これらカチオン成分に対するアニオン成分としてのルイス酸はＰＦ６ −、ＳｂＦ６ −、（Ｃ６Ｆ５）４Ｂ−、ＢＦ４ −等が挙げられる。これら光カチオン重合開始剤の添加量は、エポキシ樹脂に対し、０．５から５ｐｈｒであることが好ましい。 Examples of the cationic photopolymerization initiator include diazonium salts, sulfonium salts, iodonium salts, and the like. Examples of Lewis acids as anionic components for these cationic components include PF 6 − , SbF 6 − , (C 6 F 5 ) 4 B − and BF 4 − . The addition amount of these cationic photopolymerization initiators is preferably 0.5 to 5 phr with respect to the epoxy resin.
以下に、本発明を実施例により更に具体的に説明するが、本発明はこれら実施例に限定されるものではない。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
実施例１〜３
表１に示す組成に従って、芳香族系エポキシ樹脂であるビスフェノールＡジグリシジルエーテル（ジャパンエポキシレジン社製エピコート８２８）と脂肪族系エポキシ樹脂であるポリエチレングリコールジグリシジルエーテル（ナガセケムテック社製デナコールＥＸ８３２）及び帯電防止剤としてグリシジルトリメチルアンモニウムビストリフルオロメタンスルホニルイミドを添加して均一となるように混合し、帯電防止樹脂組成物を調整した。その後、硬化剤にＮ−アミノエチルピペラジンを２０ｐｈｒ添加し、２５℃で７日間放置して硬化させた。得られた成形体について、以下に示した試験方法にて評価した。
Examples 1-3
According to the composition shown in Table 1, aromatic epoxy resin bisphenol A diglycidyl ether (Epicoat 828 manufactured by Japan Epoxy Resin Co., Ltd.) and aliphatic epoxy resin polyethylene glycol diglycidyl ether (Denacol EX832 manufactured by Nagase Chemtech Co., Ltd.) In addition, glycidyltrimethylammonium bistrifluoromethanesulfonylimide was added as an antistatic agent and mixed uniformly to prepare an antistatic resin composition. Thereafter, 20 phr of N-aminoethylpiperazine was added to the curing agent and allowed to cure at 25 ° C. for 7 days. About the obtained molded object, it evaluated by the test method shown below.
（表面抵抗の測定）
ＮＦＰＡ試験法に準じて、成形体の表面抵抗を定格電圧５００Ｖにて測定した。また、表面抵抗測定後に水と１時間接触させた後、６０℃、１時間乾燥後に再度表面抵抗を測定した。結果を表１に示す。
(Measurement of surface resistance)
According to the NFPA test method, the surface resistance of the molded body was measured at a rated voltage of 500V. Moreover, after making surface resistance measurement, after making it contact with water for 1 hour, the surface resistance was measured again after drying at 60 degreeC for 1 hour. The results are shown in Table 1.
（引っ張り強さ測定）
日本工業規格ＪＩＳＫ６９１１に準じて、引っ張り強さを測定した。結果を表１に示す。
(Tensile strength measurement)
The tensile strength was measured according to Japanese Industrial Standard JISK6911. The results are shown in Table 1.
実施例１〜３で得られた成形体は良好な引っ張り強度を有しており、表面抵抗値も硬化後、水との接触後も良好であった。 The molded bodies obtained in Examples 1 to 3 had good tensile strength, and the surface resistance value was also good after curing and contact with water.
比較例１〜３
表１に示す組成に従い、実施例１〜３においてグリシジルトリメチルアンモニウムビストリフルオロメタンスルホニルイミドの代わりに、過塩素酸リチウムを用い、樹脂組成物を調整した。この時、過塩素酸リチウムの添加方法は、ポリエチレングリコールジグリシジルエーテルを６０℃保温下に少量づつ添加溶解して調整し、これにビスフェノールＡジグリシジルエーテルを加える方法で調整した。実施例１〜３に準じて表面抵抗、引っ張り強さを評価した。水との接触後は表面抵抗値が大きく上昇していた。
Comparative Examples 1-3
According to the composition shown in Table 1, in Examples 1 to 3, a resin composition was prepared using lithium perchlorate instead of glycidyltrimethylammonium bistrifluoromethanesulfonylimide. At this time, the method for adding lithium perchlorate was adjusted by adding and dissolving polyethylene glycol diglycidyl ether in small portions while keeping at 60 ° C., and adding bisphenol A diglycidyl ether thereto. Surface resistance and tensile strength were evaluated according to Examples 1 to 3. The surface resistance value increased greatly after contact with water.
＊２：過塩素酸リチウム
実施例４
脂肪族系エポキシ樹脂として、ダイセイル化学社製 エポリード３０１を１００質量部、グリシジルトリメチルアンモニウムビストリフルオロメタンスルホニルイミド２０質量部、スルホニウム系光カチオン重合開始剤としてユニオンカーバイド社製 ＵＶＩ−６９９０を３質量部混合し、バーコーターにてＰＥＴフィルム上に１０μｍの厚さに塗布した。直ちに高圧水銀灯にて紫外線照射により硬化させてエポキシハードコート膜を得た。得られた膜について、鉛筆硬度（日本工業規格ＪＩＳＫ５４００に準拠）、表面抵抗値（ＮＦＰＡ試験法に準拠）、耐熱性（１００℃×１時間後のフィルムの色調を目視にて比較）を調べた。得られた結果を表２に示す。
Example 4
As an aliphatic epoxy resin, 100 parts by mass of Epadide 301 manufactured by Daisail Chemical Co., Ltd., 20 parts by mass of glycidyltrimethylammonium bistrifluoromethanesulfonylimide, and 3 parts by mass of UVI-6990 manufactured by Union Carbide as a sulfonium-based photocationic polymerization initiator were mixed. And it apply | coated to the thickness of 10 micrometers on PET film with the bar coater. Immediately after curing by ultraviolet irradiation with a high-pressure mercury lamp, an epoxy hard coat film was obtained. About the obtained film | membrane, pencil hardness (conforms to Japanese Industrial Standard JISK5400), surface resistance value (conforms to NFPA test method), and heat resistance (compare the color tone of the film after 100 degreeC x 1 hour visually). . The obtained results are shown in Table 2.
比較例４
脂肪族系エポキシ樹脂として、ダイセイル化学社製 エポリード３０１を１００質量部、グリシジルトリメチルアンモニウムクロリドを２０質量部、スルホニウム系光カチオン重合開始剤としてユニオンカーバイド社製 ＵＶＩ−６９９０を３質量部混合し、均一に混合するため２-ブタノンを添加混合した。バーコーターにてＰＥＴフィルム上に１０μｍの厚さに塗布した。溶媒除去のため恒温槽にて溶媒除去した後に高圧水銀灯にて、紫外線照射により硬化させてエポキシハードコート膜を得た。実施例４同様に鉛筆硬度、表面抵抗値、耐熱性（１００℃×１時間後のフィルムの色調を目視にて比較）を調べた。得られた結果を表２に示す。
Comparative Example 4
As an aliphatic epoxy resin, 100 parts by mass of Epadide 301 manufactured by Daisail Chemical Co., Ltd., 20 parts by mass of glycidyltrimethylammonium chloride, and 3 parts by mass of UVI-6990 manufactured by Union Carbide Co. as a sulfonium-based photocationic polymerization initiator were mixed. 2-butanone was added and mixed. It apply | coated to the thickness of 10 micrometers on PET film with the bar coater. After removing the solvent in a thermostatic bath for removing the solvent, it was cured by ultraviolet irradiation with a high pressure mercury lamp to obtain an epoxy hard coat film. In the same manner as in Example 4, the pencil hardness, the surface resistance value, and the heat resistance (100 ° C. × 1 hour film color tone visually compared) were examined. The obtained results are shown in Table 2.
Claims (5)
A molded product obtained by curing the antistatic epoxy resin composition according to claim 1 or 2 with ultraviolet or electron beam using a photocationic polymerization initiator as a curing agent.
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| JP2005194502A JP2007009124A (en) | 2005-07-04 | 2005-07-04 | Antistatic epoxy resin composition and molded article |
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| JP2007045940A (en) * | 2005-08-10 | 2007-02-22 | Dainippon Ink & Chem Inc | Water-based epoxy resin composition |
| WO2009014270A1 (en) * | 2007-07-26 | 2009-01-29 | Ajinomoto Co., Inc. | Resin composition |
| JP2009209219A (en) * | 2008-02-29 | 2009-09-17 | Sanyo Chem Ind Ltd | Conductive resin composition and antistatic resin composition |
| JP2010150356A (en) * | 2008-12-25 | 2010-07-08 | Jsr Corp | Ionic functional group-containing epoxy resin |
| WO2014038810A1 (en) * | 2012-09-04 | 2014-03-13 | 동우화인켐 주식회사 | Adhesive composition |
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| JPWO2023276814A1 (en) * | 2021-06-29 | 2023-01-05 | ||
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007045940A (en) * | 2005-08-10 | 2007-02-22 | Dainippon Ink & Chem Inc | Water-based epoxy resin composition |
| JP2015221900A (en) * | 2007-07-26 | 2015-12-10 | 味の素株式会社 | Resin composition |
| JPWO2009014270A1 (en) * | 2007-07-26 | 2010-10-07 | 味の素株式会社 | Resin composition |
| US9018321B2 (en) | 2007-07-26 | 2015-04-28 | Ajinomoto Co., Inc. | Resin composition |
| KR101547874B1 (en) * | 2007-07-26 | 2015-08-27 | 아지노모토 가부시키가이샤 | Resin composition |
| WO2009014270A1 (en) * | 2007-07-26 | 2009-01-29 | Ajinomoto Co., Inc. | Resin composition |
| JP2009209219A (en) * | 2008-02-29 | 2009-09-17 | Sanyo Chem Ind Ltd | Conductive resin composition and antistatic resin composition |
| JP2010150356A (en) * | 2008-12-25 | 2010-07-08 | Jsr Corp | Ionic functional group-containing epoxy resin |
| WO2014038810A1 (en) * | 2012-09-04 | 2014-03-13 | 동우화인켐 주식회사 | Adhesive composition |
| CN104945849A (en) * | 2015-06-26 | 2015-09-30 | 苏州荣昌复合材料有限公司 | Method for preparing anti-static modified plastics |
| JPWO2023276814A1 (en) * | 2021-06-29 | 2023-01-05 | ||
| WO2023276814A1 (en) * | 2021-06-29 | 2023-01-05 | ナミックス株式会社 | Epoxy resin composition, semiconductor device, and method for producing semiconductor device |
| CN116041667A (en) * | 2021-10-28 | 2023-05-02 | 中国石油化工股份有限公司 | Method for synthesizing bisphenol A type liquid epoxy resin by catalysis of composite catalyst |
| CN116196980A (en) * | 2022-09-09 | 2023-06-02 | 天津市职业大学 | Ionic liquid modified epoxy resin-based immobilized metal salt catalyst and its preparation method and application |
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