JP2011057588A - 多価ヒドロキシ化合物、それらの製造方法及びエポキシ樹脂組成物並びにその硬化物 - Google Patents
多価ヒドロキシ化合物、それらの製造方法及びエポキシ樹脂組成物並びにその硬化物 Download PDFInfo
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- JP2011057588A JP2011057588A JP2009207182A JP2009207182A JP2011057588A JP 2011057588 A JP2011057588 A JP 2011057588A JP 2009207182 A JP2009207182 A JP 2009207182A JP 2009207182 A JP2009207182 A JP 2009207182A JP 2011057588 A JP2011057588 A JP 2011057588A
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- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 150000002440 hydroxy compounds Chemical class 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 84
- 125000005462 imide group Chemical group 0.000 claims abstract description 52
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 36
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 31
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 150000002989 phenols Chemical class 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 150000001299 aldehydes Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- AJXNLGUENUIIRW-UHFFFAOYSA-N naphtho[2,3-f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C(C=C3C(=O)OC(=O)C3=C3)C3=CC2=C1 AJXNLGUENUIIRW-UHFFFAOYSA-N 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
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- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- 125000006839 xylylene group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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Abstract
Description
(但し、R1は水素原子、水酸基、炭素数1〜8のアルコキシ基又は炭素数1〜8の炭化水素基を示し、R2〜R4は水素原子又は炭素数1〜8の炭化水素基を示し、Xは直接結合、−O−、−S−、−SO2−、−CO−又は二価の炭化水素基を示す。nは1〜10の数であり、mは0〜2の整数であるが、mの平均は0.05〜1.5である。)
(但し、R1は水素原子、水酸基、炭素数1〜8のアルコキシ基又は炭素数1〜8の炭化水素基を示し、Xは直接結合、−O−、−S−、−SO2−、−CO−又は二価の炭化水素基を示す。nは1〜10の数である。)
(但し、R2、R3は水素原子又は炭素数1〜8の炭化水素基を示す。)
(但し、R4は水素原子又は炭素数1〜8の炭化水素基を示す。)
(但し、R1〜R4、X、n及びmは、一般式(1)と同じ意味を有する。Zはジカルボン酸無水物類から生じる少なくとも2個の炭素原子を有する2価の基である。)
1)硬化剤の一部又は全部として前記アミノ基含有樹脂を配合した組成物。
2)硬化剤の一部又は全部として前記イミド基含有樹脂を配合した組成物。
3)硬化剤の一部又は全部として前記アミノ基含有樹脂と前記イミド基含有樹脂を配合した組成物。
ここで、粘度はBROOKFIELD製、CAP2000Hを用い、軟化点はJIS K−6911に従い環球法で測定した。また、GPC測定は、装置;日本ウォーターズ(株)製、515A型、カラム;TSK−GEL2000×3本およびTSK−GEL4000×1本(いずれも東ソー(株)製)、溶媒;テトラヒドロフラン、流量;1 ml/min、温度;38℃、検出器;RIの条件であり、検量線にはポリスチレン標準液を使用した。アミン当量は0.1M過塩素酸−酢酸溶液による電位差滴定により求めた。また、アミノ基含有樹脂の水酸基当量は、塩化アセチル法で求めた水酸基とアミノ基の合計量から、アミン当量の測定で求めたアミノ基量を差し引くことで水酸基量を見積もることで推算した。
アニリン46.5g(0.5モル)、4,4’−ジヒドロキシジフェニルメタン200g(1.0モル)を仕込み、窒素を導入しながら80℃に加熱し、37%ホルマリン水溶液40.5g(0.5モル)を滴下した。次に、撹拌しながら95℃まで昇温して2時間還流させ、さらに脱水後180℃まで昇温し、2時間反応させた。その後、減圧下180℃にて未反応のアニリンを除去し、アミノ基含有樹脂238.5gを得た。得られた樹脂の水酸基当量は117.4g/eq.、アミン当量は626.4g/eq.、軟化点は62℃、150℃における溶融粘度は31mPa・sであった。
実施例1で得られたアミノ基含有樹脂60g、無水フタル酸14.2gを仕込み、窒素を導入しながら150℃に加熱し溶解させ1時間反応させた。この間、反応により生成する水は系外に除いた。その後、減圧下230℃にて未反応の無水フタル酸を除去し、イミド基含有樹脂57.1gを得た(樹脂A)。得られた樹脂の水酸基当量は157g/eq.、アミン当量は74950g/eq.、軟化点は76℃、150℃における溶融粘度は0.11Pa・sであった。
実施例1で得られたアミノ基含有樹脂60g、無水マレイン酸9.4g、トルエン120gを仕込み、窒素を導入しながら、110℃に加熱してトルエンとの共沸で水を系外に除きながら2時間反応させた。その後、減圧下180℃まで加熱し、トルエンおよび未反応の無水マレイン酸を除去し、イミド基含有樹脂64.3gを得た(樹脂B)。得られた樹脂の水酸基当量は144g/eq.、アミン当量は138400g/eq.、軟化点は88.5℃、150℃における溶融粘度は0.44Pa・sであった。GPCチャートを図9に示す。
アニリン46.5g(0.5モル)、4,4’−ジヒドロキシジフェニルメタン100g(0.5モル)を仕込み、窒素を導入しながら80℃に加熱し、37%ホルマリン水溶液40.5g(0.5モル)を滴下した。次に、撹拌しながら95℃まで昇温して2時間還流させ、さらに脱水後180℃まで昇温し、2時間反応させた。その後、減圧下180℃にて未反応アニリンを除去し、アミノ基含有樹脂134.6gを得た。得られた樹脂の水酸基当量は122.0g/eq.、アミン当量は386.4g/eq.、軟化点は85℃、150℃における溶融粘度は0.19Pa・sであった。GPCチャートを図10に示す。
実施例4で得られたアミノ基含有樹脂50g、無水フタル酸19.2gを仕込み、窒素を導入しながら150℃に加熱し溶解させ1時間反応させた。この間、反応により生成する水は系外に除いた。その後、減圧下230℃にて未反応無水フタル酸を除去し、イミド基含有樹脂63.8gを得た(樹脂C)。得られた樹脂の水酸基当量は189g/eq.、アミン当量は11030g/eq.、軟化点は111.3℃、150℃における溶融粘度は2.3Pa・sであった。GPCチャートを図11に示す。
アニリン45.9g(0.49モル)、ビスフェノールA150g(0.66モル)を仕込み、窒素を導入しながら80℃に加熱し、37%ホルマリン水溶液40.0g(0.49モル)を滴下した。次に、撹拌しながら95℃まで昇温して2時間還流させ、さらに脱水後180℃まで昇温し、2時間反応させた。その後、減圧下180℃にて未反応アニリンを除去し、アミノ基含有樹脂186.6gを得た。得られた樹脂の水酸基当量は132.4g/eq.、アミン当量は516.2g/eq.、軟化点は88℃、150℃における溶融粘度は0.19Pa・sであった。GPCチャートを図12に示す。
実施例6で得られたアミノ基含有樹脂70g、無水フタル酸20.1gを仕込み、窒素を導入しながら150℃に加熱し溶解させ1時間反応させた。この間、反応により生成する水は系外に除いた。その後、減圧下230℃にて未反応無水フタル酸を除去し、イミド基含有樹脂80.5gを得た(樹脂D)。得られた樹脂の水酸基当量は200g/eq.、アミン当量は39630g/eq.、軟化点は105℃、150℃における溶融粘度は1.3Pa・sであった。GPCチャートを図13に示す。
アニリン23.7g(0.25モル)、フェノールアラルキル樹脂(明和化成製、MEH−7800SS、OH当量175、軟化点67℃)200gを仕込み、窒素を導入しながら80℃に加熱し、37%ホルマリン水溶液20.6g(0.25モル)を滴下した。次に、撹拌しながら95℃まで昇温して2時間還流させ、さらに脱水後180℃まで昇温し、2時間反応させた。その後、減圧下180℃にて未反応アニリンを除去し、アミノ基含有樹脂200gを得た。アミン当量は1060g/eqであった。GPCチャートを図14に示す。
アニリン40.0g、フェノール200.0g、37%ホルマリン溶液41.5gを仕込み、窒素を導入しながら80℃に加熱し溶解させた。次に、撹拌しながら95℃まで昇温して2時間還流させ、さらに脱水後180℃まで昇温し、2時間反応させた。その後、減圧下180℃にて未反応フェノール、アニリンを除去し、アミノ基含有樹脂102.0gを得た。得られた樹脂の水酸基当量は145.8g/eq.、アミン当量は242g/eq.、軟化点は61℃、150℃における溶融粘度は0.02Pa・sであった。
エポキシ樹脂成分としてo-クレゾールノボラック型エポキシ樹脂(エポキシ当量200、軟化点65℃)、硬化剤として実施例2、3、5、7、8、合成例1で得たイミド基含有樹脂(樹脂A〜F)、フェノールノボラック(樹脂G:群栄化学製、PSM−4261;OH当量103、軟化点 82℃)、フェノールアラルキル樹脂(樹脂H;明和化成製、MEH−7800SS、OH当量175、軟化点67℃)を用い、充填剤としてシリカ(平均粒径18μm)、硬化促進剤としてトリフェニルホスフィン及び表1に示すその他の成分を表1に示す配合割合で混練しエポキシ樹脂組成物を得た。このエポキシ樹脂組成物を用いて175℃にて成形し、175℃にて12時間ポストキュアを行い、硬化物試験片を得た後、各種物性測定に供した。
Claims (6)
- 下記一般式(2)、
(但し、R1は水素原子、水酸基、炭素数1〜8のアルコキシ基又は炭素数1〜8の炭化水素基を示し、Xは直接結合、−O−、−S−、−SO2−、−CO−又は二価の炭化水素基を示す。nは1〜10の数である。)で表されるフェノール類の水酸基を有するベンゼン環1モルに対して、
下記一般式(3)、
(但し、R2、R3は水素原子又は炭素数1〜8の炭化水素基を示す。)
で表される芳香族アミン類を0.05〜1.5モル、
下記一般式(4)、
(但し、R4は水素原子又は炭素数1〜8の炭化水素基を示す。)
で表されるアルデヒド類を0.05〜1.5モル用い、かつ芳香族アミン類とアルデヒド類のモル比が0.5〜2.0の条件で反応させることを特徴とするアミノ基含有多価ヒドロキシ化合物の製造方法。 - 下記一般式(2)で表されるフェノール類中の水酸基を有するベンゼン環1モルに対して、下記一般式(3)で表される芳香族アミン類を0.05〜1.5モル、下記一般式(4)で表されるアルデヒド類を0.05〜1.5モル用い、かつ芳香族アミン類とアルデヒド類のモル比が0.5〜2.0の条件で反応させることによりアミノ基含有多価ヒドロキシ化合物を得て、次にこのアミノ基含有多価ヒドロキシ化合物とZ(CO)2O(但し、Zは少なくとも2個の炭素原子を有する2価の基である。)で表わされるジカルボン酸無水物類を、アミノ基1モルに対し酸無水物基が1.0〜1.5モルとなる割合で使用して反応させることを特徴とするイミド基含有多価ヒドロキシ化合物の製造方法。
(但し、R1は水素原子、水酸基、炭素数1〜8のアルコキシ基又は炭素数1〜8の炭化水素基を示し、Xは直接結合、−O−、−S−、−SO2−、−CO−又は二価の炭化水素基を示す。nは1〜10の数である。)
(但し、R2、R3は水素原子又は炭素数1〜8の炭化水素基を示す。)
(但し、R4は水素原子又は炭素数1〜8の炭化水素基を示す。) - エポキシ樹脂及び硬化剤よりなるエポキシ樹脂組成物において、硬化剤の一部又は全部として、請求項1又は3に記載のアミド基含有多価ヒドロキシ化合物又はイミド基含有多価ヒドロキシ化合物を用いることを特徴とするエポキシ樹脂組成物。
- 請求項5に記載のエポキシ樹脂組成物を硬化してなるエポキシ樹脂硬化物。
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JP2009207182A JP5462559B2 (ja) | 2009-09-08 | 2009-09-08 | 多価ヒドロキシ化合物、それらの製造方法及びエポキシ樹脂組成物並びにその硬化物 |
TW099128274A TWI510454B (zh) | 2009-09-08 | 2010-08-24 | A polyhydroxy compound, a method for producing the same, and an epoxy resin composition, and a hardened product thereof |
KR1020100085922A KR20110027580A (ko) | 2009-09-08 | 2010-09-02 | 다가 히드록시화합물, 그들의 제조방법 및 에폭시수지 조성물 및 그 경화물 |
CN201010275389.2A CN102010343B (zh) | 2009-09-08 | 2010-09-08 | 多元羟基化合物及其制造方法和环氧树脂组合物及其固化物 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012011541A1 (ja) | 2010-07-22 | 2012-01-26 | 凸版印刷株式会社 | カセット取付装置及びカセット |
CN104163903A (zh) * | 2013-05-17 | 2014-11-26 | 和新化学工业股份有限公司 | 含磷的酚树脂、其制造方法及其用途 |
Families Citing this family (4)
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MY169844A (en) * | 2012-02-23 | 2019-05-17 | Nippon Steel Chemical & Mat Co Ltd | Polyvalent hydroxy resin, epoxy resin, method for producing same, epoxy resin composition and cured product thereof |
KR101596992B1 (ko) * | 2012-06-26 | 2016-02-23 | 코오롱인더스트리 주식회사 | 비할로겐 난연성 중합체 및 이를 함유하는 난연성 중합체 조성물 |
KR101598244B1 (ko) * | 2012-06-26 | 2016-02-26 | 코오롱인더스트리 주식회사 | 비할로겐 난연성 중합체 및 이를 함유하는 난연성 중합체 조성물 |
CN114773556B (zh) * | 2020-12-30 | 2024-06-04 | 耀科新材料(苏州)有限公司 | 一种共价有机框架材料的绿色固相合成方法 |
Citations (2)
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JPH04227624A (ja) * | 1990-03-27 | 1992-08-17 | Sumitomo Durez Co Ltd | エポキシ樹脂硬化剤及びエポキシ樹脂組成物 |
JP2003327646A (ja) * | 2002-05-07 | 2003-11-19 | Gun Ei Chem Ind Co Ltd | アミノ基含有フェノール誘導体 |
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JPH10259248A (ja) * | 1997-01-20 | 1998-09-29 | Hitachi Chem Co Ltd | 熱硬化性組成物及びその硬化物 |
MY142518A (en) * | 2001-01-10 | 2010-12-15 | Hitachi Chemical Co Ltd | Dihydrobenzoxazine ring-containing resin, phenolic-triazine-aldehyde condensate and epoxy resin |
CN1816580B (zh) * | 2003-02-03 | 2010-04-28 | 新日铁化学株式会社 | 环氧树脂、其制造方法、使用该环氧树脂的环氧树脂组合物以及固化物 |
JP2005225908A (ja) * | 2004-02-10 | 2005-08-25 | Hitachi Chem Co Ltd | プリプレグおよびプリント配線板用積層板 |
JP2006056969A (ja) * | 2004-08-19 | 2006-03-02 | Nippon Steel Chem Co Ltd | エポキシ樹脂組成物およびその硬化物 |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH04227624A (ja) * | 1990-03-27 | 1992-08-17 | Sumitomo Durez Co Ltd | エポキシ樹脂硬化剤及びエポキシ樹脂組成物 |
JP2003327646A (ja) * | 2002-05-07 | 2003-11-19 | Gun Ei Chem Ind Co Ltd | アミノ基含有フェノール誘導体 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012011541A1 (ja) | 2010-07-22 | 2012-01-26 | 凸版印刷株式会社 | カセット取付装置及びカセット |
CN104163903A (zh) * | 2013-05-17 | 2014-11-26 | 和新化学工业股份有限公司 | 含磷的酚树脂、其制造方法及其用途 |
Also Published As
Publication number | Publication date |
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KR20110027580A (ko) | 2011-03-16 |
JP5462559B2 (ja) | 2014-04-02 |
CN102010343A (zh) | 2011-04-13 |
CN102010343B (zh) | 2014-10-22 |
TW201125838A (en) | 2011-08-01 |
TWI510454B (zh) | 2015-12-01 |
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