JP2008222908A - エポキシ樹脂組成物、その硬化物、塗料用組成物、及び新規エポキシ樹脂 - Google Patents
エポキシ樹脂組成物、その硬化物、塗料用組成物、及び新規エポキシ樹脂 Download PDFInfo
- Publication number
- JP2008222908A JP2008222908A JP2007064979A JP2007064979A JP2008222908A JP 2008222908 A JP2008222908 A JP 2008222908A JP 2007064979 A JP2007064979 A JP 2007064979A JP 2007064979 A JP2007064979 A JP 2007064979A JP 2008222908 A JP2008222908 A JP 2008222908A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- resin composition
- hydrogen atom
- carbon atoms
- alkyl group
- 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
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 184
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 184
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 238000000576 coating method Methods 0.000 title claims description 24
- 239000011248 coating agent Substances 0.000 title claims description 21
- 239000002904 solvent Substances 0.000 claims abstract description 56
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 46
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 14
- 239000011707 mineral Substances 0.000 abstract description 14
- 238000003860 storage Methods 0.000 abstract description 7
- 239000000758 substrate Substances 0.000 abstract description 6
- 235000015096 spirit Nutrition 0.000 abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000001723 curing Methods 0.000 description 24
- 239000003973 paint Substances 0.000 description 23
- -1 aliphatic monocarboxylic acid Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000005011 phenolic resin Substances 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 229920003986 novolac Polymers 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 229920001568 phenolic resin Polymers 0.000 description 15
- 239000000835 fiber Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 239000012948 isocyanate Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 235000010755 mineral Nutrition 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 150000002989 phenols Chemical class 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- 230000007797 corrosion Effects 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000001588 bifunctional effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 150000001728 carbonyl compounds Chemical class 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 229920003180 amino resin Polymers 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000004567 concrete Substances 0.000 description 4
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004513 sizing Methods 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
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- 238000001035 drying Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 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 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
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- 239000004606 Fillers/Extenders Substances 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
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Abstract
Description
(式中、R1、R2、R3、R4は水素原子または炭素原子数1〜2のアルキル基、R5は水素原子又はメチル基、Xは炭素原子数4〜12のアルキル基を表す。)
で表される部分構造で結節した分子構造を有するエポキシ樹脂(A)、及び硬化剤(B)を必須成分とすることを特徴とするエポキシ樹脂組成物に関する。
(式中、R1、R2、R3、R4は水素原子または炭素原子数1〜2のアルキル基、R5は水素原子又はメチル基、Xは炭素原子数4〜12のアルキル基を表す。)
で表される部分構造で結節した分子構造を有するエポキシ樹脂(A)、及び脂肪族系溶剤(C)を必須成分とすることを特徴とするエポキシ樹脂組成物に関する。
(式中、R1、R2、R3、R4は水素原子または炭素原子数1〜2のアルキル基、R5は水素原子又はメチル基、Xは炭素原子数4〜12のアルキル基を表す。)
で表される部分構造で結節した分子構造を有することを特徴とする。
1)下記構造式(2)
(式中、R1、R2、R3、R4は水素原子または炭素原子数1〜2のアルキル基、R5は水素原子又はメチル基、Xは炭素原子数4〜12のアルキル基、Rはそれぞれ独立に水素原子またはメチル基を表し、nは繰り返し単位の平均値で0〜20である。)
で表される構造を有するエポキシ樹脂(a)、
3)下記構造式(3)
(式中、R1、R2、R3、R4は水素原子または炭素原子数1〜2のアルキル基、R5は水素原子又はメチル基、Xは炭素原子数4〜12のアルキル基を表す。)
に表されるフェノール系樹脂(A’)と2官能性エポキシ樹脂とを反応させて得られたエポキシ樹脂(c)、及び、
4)前記構造式(3)に表されるフェノール系樹脂(A’)と、2官能性フェノールと、2官能性エポキシ樹脂とを反応させて得られたエポキシ樹脂(d)、
が挙げられる。
で表されるものである。該構造式(3)中、R1、R2、R3、R4は、前記した通り、水素原子、または、メチル基、エチル基、プロピル基、i−プロピル基、ブチル基等の炭素原子数1〜4のアルキル基であるが、次工程である工程(II)におけるエピハロヒドリン類(a3)との反応性が良好となる点から、水素原子又はメチル基であることが好ましく、特にメチル基であることが好ましい。また、前記構造式(3)中のR5は水素原子又はメチル基であり、Xはメチル基、イソブチル基、ブチル基、オクチル基、デカン基、ドデシル基等の炭素原子数4〜12のアルキル基を表す。
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに下記構造式p1で表されるフェノール類(本州化学工業株式会社「Bis−DED」、水酸基当量163g/eq.)163g、エピクロルヒドリン370g(4モル)、n−ブタノール222gを仕込み溶解させた。その後、窒素ガスパージを施しながら、65℃に昇温した後に、共沸する圧力までに減圧して、49質量%水酸化ナトリウム水溶液122g(1.5モル)を5時間かけて滴下した。次いでこの条件下で0.5時間撹拌を続けた。この間、共沸で留出してきた留出分をディーンスタークトラップで分離して、水層を除去し、有機層を反応系内に戻しながら反応した。その後、常圧に戻し、水240gを仕込み生成した塩を洗浄した。洗浄後、未反応のエピクロルヒドリンを減圧蒸留して留去した。次いで得られた粗エポキシ樹脂にメチルイソブチルケトン1000gを加え溶解した。その後、中和量のリン酸ソーダを添加し、次いで共沸によって系内を脱水し精密濾過を経た後に溶媒を減圧下で留去して液状のエポキシ樹脂212gを得た(以下、このエポキシ樹脂を「エポキシ樹脂(Ep−1)」と略記する。)。このエポキシ樹脂(Ep−1)は、NMRスペクトル(13C)から、またマススペクトルで下記構造式e1の理論構造(n=0)に相当するM+=438のピークが得られたことから下記構造式e1で表されるエポキシ樹脂を含有することが確認された。このエポキシ樹脂(Ep−1)のエポキシ当量は240g/eq.、粘度は1580mm2/s(25℃,キャノンフェンスケ法)、エポキシ当量から算出される下記構造式(e1)中のnは繰り返し単位の平均であり、その値は0.1であった。
エポキシ樹脂(Ep−1)のNMRスペクトル(13C)のチャート図を図1に、マススペクトルのチャート図を図2に示す。
実施例1において、用いる原料をフェノール類(本州化学工業株式会社「Bis−DED」、水酸基当量163g/eq.)163gから下記構造式p2で表されるフェノール類(本州化学工業株式会社「Bis−MIBK」、水酸基当量135g/eq.)135gに変更した以外は実施例1と同様の操作にて液体のエポキシ樹脂195gを得た(以下、このエポキシ樹脂を「エポキシ樹脂(Ep−2)」と略記する。)。このエポキシ樹脂(Ep−2)は、NMRスペクトル(13C)から、またマススペクトルで実施例1と同様にM+=382のピークが得られたことか下記構造式e2で表される構造のエポキシ樹脂を含有することが確認された。このエポキシ樹脂(Ep−2)のエポキシ当量は207g/eq.、粘度は30250mm2/s(25℃,キャノンフェンスケ法)、エポキシ当量から算出される下記構造式(e2)中のnの値は0.1であった。エポキシ樹脂(Ep−2)のNMRスペクトル(13C)のチャート図を図3に、マススペクトルのチャート図を図4に示す。
実施例1において、用いる原料をエピクロルヒドリン370g(4モル)からエピクロルヒドリン65g(0.7モル)に変更した以外は実施例1と同様の操作にて半固形のエポキシ樹脂190gを得た(以下、このエポキシ樹脂を「エポキシ樹脂(Ep−3)」と略記する。)。このエポキシ樹脂(Ep−3)のエポキシ当量は690g/eq.、25℃で半固形、エポキシ当量から算出される上記構造式(e2)中のnの値は2.3であった。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、実施例1で得られたエポキシ樹脂(Ep−1)576g、ビスフェノールA(水酸基当量114g/eq)228gを仕込み、140℃まで30分間要して昇温した後、4%水酸化ナトリウム水溶液10gを仕込んだ。その後、30分間要して150℃まで昇温し、さらに150℃で8時間反応させた。その後、中和量のリン酸ソーダを添加し、エポキシ樹脂800gを得た(以下、このエポキシ樹脂を「エポキシ樹脂(Ep−4)」と略記する。)。このエポキシ樹脂(Ep−4)のエポキシ当量は2010g/eq.、25℃で半固形であった。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、ノニルフェノール660gと37%ホルマリン水溶液162gとトルエン155gを仕込み、100℃に昇温して攪拌均一化した。その後、蓚酸7gを発熱に注意しながら仕込み、150℃で2時間反応を行った後、トルエンを蒸留回収することによって平均官能基数3のノニルフェノールノボラック樹脂を得た。ついでBPA型エポキシ樹脂(大日本インキ化学工業株式会社製「EPICLON 850」、エポキシ当量186g/eq.)930gと不揮発分60質量%となる量のミネラルスピリットを添加し、110℃に昇温しながら攪拌均一化した。その後、水酸化カリウムを全樹脂量に対し0.01wt%添加し、さらに150℃まで昇温して固形成分のエポキシ当量が665g/eq.になるまで反応させた。このエポキシ樹脂を(E’−1)のと略記する。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコにオルソクレゾールノボラック型エポキシ樹脂(大日本インキ化学工業株式会社製「EPICLON N−680」エポキシ当量213g/eq.)300gとBPA型エポキシ樹脂(大日本インキ化学工業株式会社製「EPICLON 850」、エポキシ当量186g/eq.)60g及びトール油脂肪酸238gを仕込んだ。撹拌を行いながら100℃まで昇温し、触媒として、エチルトリフェニルホスホニウムブロマイド0.14gを加え、さらに160℃まで昇温し、3時間反応させた。このエポキシ樹脂(E’−2)のエポキシ当量は686g/eq.であった。
上記のようにして合成された6種類のエポキシ樹脂(Ep−1)、(Ep−2)、(Ep−3)、(E’−1)、(E’−2)、BPA型エポキシ樹脂(商品名:EPICLON 2055 大日本インキ化学工業株式会社製、エポキシ当量625g/eq.)を用いて性能評価を行った。
表1記載の各エポキシ樹脂と各脂肪族系溶剤を加え攪拌均一化する事によって不揮発分50%のエポキシ樹脂組成物を得た。これを100ml容量のマヨネーズ瓶に90g量り取り、5℃の恒温漕にて保管し、1週間後の外観を目視にて観察した。
表1記載の各エポキシ樹脂に各脂肪族系溶剤をそれぞれ加え、白濁に要する溶剤の質量を求め、次式により算出した。
[粘度500mmPa・s時の不揮発分]
表1記載の各エポキシ樹脂のそれぞれを粘度が500mmPa・sになるようにミネラルスピリットに溶解した際の不揮発分。尚、粘度はキャノンフェンスケ法(25℃)にて測定した。
注1)脂肪族系溶剤としてミネラルスピリット(シェルジャパン製LAWS)を用いた。
注2)脂肪族系溶剤として0号ソルベント(日本石油(株)製、芳香族成分0.0%溶剤:沸点244〜262℃、引火点133℃)を用いた。
注3)ミネラルスピリットを溶剤に用いた際の25℃の粘度が500mmPa・sとなる不揮発分量。
次に、得られた水性エポキシ樹脂組成物を用いて表2の配合比で水性塗料を作成し、#400のサンドペーバーで表面処理を行った冷却圧延鋼板に対しバーコーターにて塗布した後、塗膜物性評価を行った。なお、表2記載の塗料はPWC=50%、塗膜物性は膜厚60μm、25℃×7日養生後の試験結果である。尚、各試験方法及び評価基準は下記の通りである。
「CR−95」:石原産業株式会社製酸化チタン「タイペークCR−95」
「BYK−341」:ビックケミー社製添加剤
Claims (8)
- 前記エポキシ樹脂(A)のエポキシ当量が200〜3100g/eq.の範囲である請求項1又は2記載のエポキシ樹脂組成物。
- 前記エポキシ樹脂(A)及び硬化剤(B)に加え、更に脂肪族系溶剤(C)を含む請求項1〜3の何れか1つに記載のエポキシ樹脂組成物。
- 前記請求項1〜4の何れか1つに記載のエポキシ樹脂組成物を硬化させてなる硬化物。
- 前記請求項1〜4の何れか1つに記載のエポキシ樹脂組成物からなる塗料用組成物。
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JPWO2015037590A1 (ja) * | 2013-09-12 | 2017-03-02 | 日本化薬株式会社 | エポキシ樹脂混合物、エポキシ樹脂組成物、硬化物および半導体装置 |
JP2021161184A (ja) * | 2020-03-31 | 2021-10-11 | ベック株式会社 | 被覆材 |
WO2023100722A1 (ja) * | 2021-11-30 | 2023-06-08 | 味の素株式会社 | エポキシ樹脂 |
JP7550194B2 (ja) | 2022-03-28 | 2024-09-12 | メモリーズ株式会社 | 故人が放置された部屋の消臭施工方法 |
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Cited By (7)
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JPWO2015037590A1 (ja) * | 2013-09-12 | 2017-03-02 | 日本化薬株式会社 | エポキシ樹脂混合物、エポキシ樹脂組成物、硬化物および半導体装置 |
KR20210031539A (ko) * | 2013-09-12 | 2021-03-19 | 닛뽄 가야쿠 가부시키가이샤 | 에폭시 수지 혼합물, 에폭시 수지 조성물, 경화물 및 반도체 장치 |
KR102376061B1 (ko) | 2013-09-12 | 2022-03-18 | 닛뽄 가야쿠 가부시키가이샤 | 에폭시 수지 혼합물, 에폭시 수지 조성물, 경화물 및 반도체 장치 |
JP2021161184A (ja) * | 2020-03-31 | 2021-10-11 | ベック株式会社 | 被覆材 |
JP7506509B2 (ja) | 2020-03-31 | 2024-06-26 | ベック株式会社 | 被覆材 |
WO2023100722A1 (ja) * | 2021-11-30 | 2023-06-08 | 味の素株式会社 | エポキシ樹脂 |
JP7550194B2 (ja) | 2022-03-28 | 2024-09-12 | メモリーズ株式会社 | 故人が放置された部屋の消臭施工方法 |
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