JPWO2007046316A1 - エポキシ樹脂、硬化性樹脂組成物、およびその硬化物 - Google Patents
エポキシ樹脂、硬化性樹脂組成物、およびその硬化物 Download PDFInfo
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- JPWO2007046316A1 JPWO2007046316A1 JP2007540955A JP2007540955A JPWO2007046316A1 JP WO2007046316 A1 JPWO2007046316 A1 JP WO2007046316A1 JP 2007540955 A JP2007540955 A JP 2007540955A JP 2007540955 A JP2007540955 A JP 2007540955A JP WO2007046316 A1 JPWO2007046316 A1 JP WO2007046316A1
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- Prior art keywords
- epoxy resin
- epoxy
- phenol
- group
- parts
- 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.)
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 191
- 239000011342 resin composition Substances 0.000 title claims description 69
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 57
- 239000004593 Epoxy Substances 0.000 claims abstract description 31
- 150000002989 phenols Chemical class 0.000 claims abstract description 29
- 150000004780 naphthols Chemical class 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000005647 linker group Chemical group 0.000 claims abstract description 3
- 229920005989 resin Polymers 0.000 claims description 70
- 239000011347 resin Substances 0.000 claims description 70
- 239000002904 solvent Substances 0.000 claims description 49
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000003063 flame retardant Substances 0.000 claims description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- -1 n-octyl group Chemical group 0.000 description 43
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- 229930185605 Bisphenol Natural products 0.000 description 9
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 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 8
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- 229910019142 PO4 Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 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 7
- 239000000945 filler Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002460 imidazoles Chemical class 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
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- 239000003973 paint Substances 0.000 description 6
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- 229920002799 BoPET Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000011889 copper foil Substances 0.000 description 5
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- 229910052751 metal Inorganic materials 0.000 description 5
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- IFZUFHWISBKFJP-UHFFFAOYSA-N n'-[4-[dimethoxy(methyl)silyl]oxybutyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)OCCCCNCCN IFZUFHWISBKFJP-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910001656 zinc mineral Inorganic materials 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
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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Abstract
Description
(1)少なくともフェノール類またはナフトール類をアラルキル基を結合基として結合した構造及び式(1)
条件:エポキシ樹脂のエポキシ当量に対してフェノールを当モル付加させて得られるフェノール変性エポキシ樹脂の水酸基当量をA(JIS K 0070に準拠して測定)、該エポキシ樹脂のエポキシ当量をBとした場合に両者の関係が下記関係式(α)を満たす。
(2)下記一般式(2)
を表し、互いに同一でも異なっていてもよく、異なっている場合は任意の順で配列していてもよい。nは1〜10の繰り返し数の平均値を表す。]
で表される構造のフェノールアラルキル樹脂とエピハロヒドリンとの反応生成物である、上記(1)に記載のエポキシ樹脂、
(3)全てのRが水素原子である、上記(2)に記載のエポキシ樹脂、
(4)全てのArが式(3)のフェノール類である上記(2)または(3)に記載のエポキシ樹脂、
(5)上記(1)〜(4)のいずれか一項に記載のエポキシ樹脂及び溶剤を含有することを特徴とするエポキシ樹脂ワニス、
(6)上記(1)〜(4)のいずれか一項に記載のエポキシ樹脂及び硬化剤を含有することを特徴とする硬化性樹脂組成物、
(7)上記(1)〜(4)のいずれか一項に記載のエポキシ樹脂及びシアネート樹脂もしくはそのプレポリマーを含有することを特徴とする硬化性樹脂組成物、
(8)上記(6)または(7)に記載の硬化性樹脂組成物を硬化してなる硬化物、
(9)上記(5)に記載のエポキシ樹脂ワニスまたは(6)に記載の硬化性樹脂組成物を基材に含浸させてなることを特徴とするプリプレグ、
(10)上記(9)に記載のプリプレグを1枚でまたは2枚以上重ね合わせ、加熱加圧してなることを特徴とする難燃性積層板または銅張積層板、
に関する。
を表し、互いに同一でも異なっていてもよく、異なっている場合は任意の順で配列していてもよい。nは1〜10の繰り返し数の平均値を表す。]
上記一般式(2)において、Rはそれぞれ独立して水素原子、炭素数1〜15の炭化水素基、トリフルオロメチル基、アリル基またはアリール基を表す。また、炭素数1〜15の炭化水素基としてはメチル基、エチル基、n−プロピル基、イソプロピル基、シクロプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基、イソブチル基、シクロブチル基、n−ペンチル基、イソペンチル基、ネオペンチル基、tert−ペンチル基、シクロペンチル基、n−ヘキシル基、イソヘキシル基、シクロヘキシル基、n−ヘプチル基、シクロヘプチル基、n−オクチル基、シクロオクチル基等の鎖状または環状のアルキル基等が挙げられる。またアリール基としてはフェニル基、ナフチル基、トルイル基等が挙げられる。このうち水素原子、メチル基、アリル基またはtert−ブチル基が好ましく、特に水素原子が好ましい。Rの置換位置は特に限定されないが、水酸基のオルト位またはメタ位をそれぞれ独立してとるのが好ましい。nは平均値で1〜10を示し、1〜5.0の範囲が好ましい。
なお前記において、フェノールを当モル付加させて得られるフェノール変性エポキシ樹脂は以下の条件で反応を行ったものである。
1)エポキシ当量:JIS K−7236に準じた方法で測定した。
2)軟化点:JIS K−7234に準じた方法で測定。
3)GPCの測定条件は以下の通りである。
機種:Shodex SYSTEM−21カラム:KF−804L+KF−803L(×2本)連結溶離液:THF(テトラヒドロフラン); 1ml/min.40℃ 検出器:UV(254nm;UV−41)
サンプル:約0.4%THF溶液 (20μlインジェクト)
検量線:Shodex製標準ポリスチレン使用。
4)溶融粘度:150℃における溶融粘度、ICI コーンプレートナンバー3、
サンプル量 0.155±0.005g。
実施例1
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量230g/eq.軟化点95℃、式(2)のArは全て式(3)、Rは全て水素原子、n=3.1(平均値))230部、エピクロロヒドリン231部、メタノール35部を加え、撹拌下で溶解し、75℃にまで昇温した。次いでフレーク状の水酸化ナトリウム40部を90分かけて分割添加した後、更に70℃で1時間後反応を行った。反応終了後水300部で水洗を行い、油層からロータリーエバポレーターを用いて140℃で減圧下、過剰のエピクロルヒドリン等の溶剤を留去した。残留物にメチルエチルケトン300部、トルエン300部を加え溶解し、70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、得られた溶液をロータリーエバポレーターを用いて180℃で減圧下に溶剤を留去することで目的とするエポキシ樹脂(EP1)271部を得た。得られたエポキシ樹脂のエポキシ当量は312g/eq.、関係式(α)の値は203、軟化点は82℃、溶融粘度(150℃)1.13Pa・sであった。。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は3820g/eq.であった。
実施例2
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量215g/eq.軟化点82℃、式(2)のArは全て式(3)、Rは全て水素原子、n=2.1(平均値))215部、エピクロロヒドリン231部、メタノール23部を加え、撹拌下で溶解し、75℃にまで昇温した。次いでフレーク状の水酸化ナトリウム40部を90分かけて分割添加した後、更に70℃で1時間後反応を行った。反応終了後水300部で水洗を行い、油層からロータリーエバポレーターを用いて140℃で減圧下、過剰のエピクロルヒドリン等の溶剤を留去した。残留物にメチルエチルケトン300部、トルエン300部を加え溶解し、70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、得られた溶液をロータリーエバポレーターを用いて180℃で減圧下に溶剤を留去することで目的とするエポキシ樹脂(EP2)258部を得た。得られたエポキシ樹脂のエポキシ当量は304g/eq.、関係式(α)の値は188、軟化点は75℃、溶融粘度(150℃)0.64Pa・sであった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は2970g/eq.であった。
実施例3
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量215g/eq.軟化点82℃、式(2)のArは全て式(3)、Rは全て水素原子、n=2.1(平均値))215部、エピクロロヒドリン370部、メタノール37部を加え、撹拌下で溶解し、75℃にまで昇温した。次いでフレーク状の水酸化ナトリウム30部を90分かけて分割添加した後、更に70℃で1時間後反応を行った。反応終了後水300部で水洗を行い、油層からロータリーエバポレーターを用いて140℃で減圧下、過剰のエピクロルヒドリン等の溶剤を留去した。残留物にメチルエチルケトン300部、トルエン300部を加え溶解し、70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、得られた溶液をロータリーエバポレーターを用いて180℃で減圧下に溶剤を留去することで目的とするエポキシ樹脂(EP3)249部を得た。得られたエポキシ樹脂のエポキシ当量は310g/eq.、関係式(α)の値は167、軟化点は78℃、溶融粘度(150℃)0.82Pa・sであった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は2673g/eq.であった。
比較例1
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量249g/eq.軟化点95℃、式(2)のArは全て式(3)、Rは全て水素原子、n=6.5(平均値))249部、エピクロロヒドリン740部、メタノール74部を加え、撹拌下で溶解し、75℃にまで昇温した。次いでフレーク状の水酸化ナトリウム42部を90分かけて分割添加した後、更に70℃で1時間後反応を行った。反応終了後水300部で水洗を行い、油層からロータリーエバポレーターを用いて140℃で減圧下、過剰のエピクロルヒドリン等の溶剤を留去した。残留物にメチルエチルケトン300部、トルエン300部を加え溶解し、70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、得られた溶液をロータリーエバポレーターを用いて180℃で減圧下に溶剤等を留去することで目的とするエポキシ樹脂(EP4)301部を得た。得られたエポキシ樹脂のエポキシ当量は306g/eq.、関係式(α)の値は269、軟化点は75℃、溶融粘度(150℃)0.52Pa・sであった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は9998g/eq.であった。
比較例2
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに窒素ガスパージを施しながらエポキシ樹脂NC−3000−H(日本化薬株式会社製、エポキシ当量290g/eq、軟化点68℃、nの値2.5(平均値))290部、フェノールアラルキル樹脂MEH−7851SS(明和化成株式会社製、水酸基当量203g/eq、軟化点65℃)15部を仕込み、撹拌下150℃で完全に溶融させた後トリフェニルホスフィン0.29部を加え4時間反応させ、比較用のエポキシ樹脂(EP5)305部を得た。得られたエポキシ樹脂のエポキシ当量は328g/eq、関係式(α)の値は135、軟化点は84℃であった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は2459g/eq.であった。
試験例1〜3
得られたエポキシ樹脂EP1、EP4、および市販のNC−3000Hのデータを比較すると下記表1のようになる。なお保存安定性の試験結果はそれぞれメチルエチルケトンを溶剤として70重量%のエポキシ樹脂ワニスとし、5℃、0℃、−10℃での冷蔵保管を行ったときの評価結果を結晶が析出する時間で示した。
試験例4〜6
以下に硬化性樹脂組成物(a)の硬化物に関する評価について記載する。
DMA JIS K−7244−4
TMA 熱機械測定装置:真空理工(株)製 TM−7000
昇温速度:2℃/min.
破壊靭性(K1C):ASTM E−399
ピール強度:JIS K−6911
曲げ強度 :JIS K−6911
・シアネート化合物溶液:シアネート樹脂プレポリマーB−40S(チバガイギー社製、ビスフェノールAジシアネート樹脂、3量体含有率40重量%、固形分75重量%のMEK溶液)
・リン化合物:FP−500(旭電化株式会社 リン系難燃剤)
・バインダー樹脂:KAYAFLEX−BPAM01(日本化薬株式会社製 ゴム変性ポリアミド樹脂)
・硬化促進剤:ニッカオクチックス亜鉛8%(日本化学産業株式会社製 2−エチルヘキシル酸亜鉛ミネラルスピリット溶液)
以上の結果より、本発明のフェノールアラルキル型エポキシ樹脂は、溶剤に溶解して低温で保存しても、結晶の析出が起こりにくいため、これを利用した硬化性樹脂組成物において、長期保存後の性能の低下を防止でき、樹脂組成物の保存安定性の向上に寄与するものである。さらには得られた硬化性樹脂組成物(a)の硬化物は高い耐熱性と機械的な特性を有していることがわかる。またシアネート樹脂を使用した硬化性樹脂組成物(b)においても、耐熱性、難燃性を保持していることを示す。したがって本発明のエポキシ樹脂、および硬化性樹脂組成物は、成形材料、注型材料、積層材料、塗料、接着剤、レジストなどの広範囲の用途にきわめて有用である。
実施例1にて得られたエポキシ樹脂(EP1)、比較としてフェノール−ビフェニルアラルキル型エポキシ樹脂NC−3000(日本化薬株式会社製 エポキシ当量275g/eq.、軟化点57℃、関係式(α)の値=272)を用いて、表5に示す組成(数値は部)でエポキシ樹脂ワニスを調製した。
・剥離性評価:露光終了後を覆っていたPETフィルムを剥離除去する際の剥がれ易さ。
・耐熱性評価:絶縁層を構成した熱硬化反終了後の銅張り積層板に、クロスカット(JIS K5600−5−6:1999に準拠)を入れた後、フラックスを塗布した後290℃の半田浴に1分間浸漬した。浸漬後基板を取り出し水洗後、圧縮空気で乾燥した。絶縁層に基材への密着性をセロハンテープ剥離試験(JIS K5600−5−6:1999)により評価した。
CCR−1194;クレゾールノボラック型酸無水物変性エポキシアクリレートKAYARAD CCR−1192(日本化薬製、メチルイソブチルケトン溶液、固形分65%、酸価100mg KOH/g)
DPCA−60;日本化薬製 カプロラクタム変性多官能アクリレート樹脂
イルガキュア907;チバスペシャリティケミカルズ製 2−メチル−(4−(メチルチオ)フェニル)−2−モルホリノ−1−プロパン
DETX−S;日本化薬製、2,4−ジエチルチオキサントン
KS−66;信越化学製、消泡剤
MIBK;メチルイソブチルケトン
実施例4
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量240g/eq.軟化点101℃、式(2)のArは全て式(3)、Rは全て水素原子、n=4.5(平均値))240部、エピクロロヒドリン277部、メタノール28部、t−ブチルアルコール28部を加え、撹拌下で溶解し、75℃にまで昇温した。次いでフレーク状の水酸化ナトリウム42部を90分かけて分割添加した後、更に70℃で1時間後反応を行った。反応終了後水300部で水洗を行い、油層からロータリーエバポレーターを用いて140℃で減圧下、過剰のエピクロルヒドリン等の溶剤を留去した。残留物にメチルエチルケトン300部、トルエン300部を加え溶解し、70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、得られた溶液をロータリーエバポレーターを用いて180℃で減圧下に溶剤を留去することで目的とするエポキシ樹脂(EP6)220部を得た。得られたエポキシ樹脂のエポキシ当量は329g/eq.、関係式(α)の値は180、軟化点は79℃であった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は3643g/eq.であった。
実施例5
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量225g/eq.軟化点84℃、式(2)のArは全て式(3)、Rは全て水素原子、n=2.2(平均値))225部、エピクロロヒドリン462部、ジメチルスルホキシド116部を加え、撹拌下で溶解し、45℃にまで昇温した。次いでフレーク状の水酸化ナトリウム41部を90分かけて分割添加した後、更に40℃で2時間、70℃で1時間後反応を行った。反応終了後、ロータリーエバポレーターを用いて減圧下、過剰のエピクロルヒドリン、ジメチルスルホキシド等の溶剤を留去した。残留物にメチルケトン250部、トルエン250部を加え溶解し、水200部で水洗し、残っている塩等を除去した後、油層を70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、油層からロータリーエバポレーターを使用し、溶剤類を約400部留去した。さらにここにフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量197g/eq.軟化点64℃、式(2)のArは全て式(3)、Rは全て水素原子、n=1.6(平均値))を14部、トリフェニルホスフィン0.3部を加え還流下40時間撹拌を行った。得られた溶液をロータリーエバポレーターを用いて180℃で減圧下に溶剤を留去することで目的とするエポキシ樹脂(EP7)260部を得た。得られたエポキシ樹脂のエポキシ当量は324g/eq.、関係式(α)の値は154、軟化点は80℃、溶融粘度(150℃)0.88Pa・sであった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は2759g/eq.であった。
実施例6
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量225g/eq.軟化点84℃、式(2)のArは全て式(3)、Rは全て水素原子、n=2.2(平均値))225部、エピクロロヒドリン462部、ジメチルスルホキシド116部を加え、撹拌下で溶解し、45℃にまで昇温した。次いでフレーク状の水酸化ナトリウム41部を90分かけて分割添加した後、更に40℃で2時間、70℃で1時間後反応を行った。反応終了後、ロータリーエバポレーターを用いて減圧下、過剰のエピクロルヒドリン、ジメチルスルホキシド等の溶剤を留去した。残留物にメチルケトン250部、トルエン250部を加え溶解し、水200部で水洗し、残っている塩等を除去した後、油層を70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、油層からロータリーエバポレーターを使用し、溶剤類を留去することで樹脂状のエポキシ樹脂(EP8)が得られた。得られたエポキシ樹脂(EP8)はエポキシ当量288g/eq.、関係式(α)の値は270、軟化点は69℃、溶融粘度(150℃)0.31Pa・sであった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は6376g/eq.であった。
比較例3
撹拌機、温度計、コンデンサが装着されたフラスコに窒素ガスパージしながらフェノールアラルキル樹脂(特許文献3に記載の方法に準じて合成。水酸基当量225g/eq.軟化点84℃、式(2)のArは全て式(3)、Rは全て水素原子、n=2.2(平均値))225部、エピクロロヒドリン462部、ジメチルスルホキシド116部を加え、撹拌下で溶解し、45℃にまで昇温した。次いでフレーク状の水酸化ナトリウム41部を90分かけて分割添加した後、更に40℃で2時間、70℃で1時間後反応を行った。反応終了後、ロータリーエバポレーターを用いて減圧下、過剰のエピクロルヒドリン、ジメチルスルホキシド等の溶剤を留去した。残留物にメチルケトン250部、トルエン250部を加え溶解し、水200部で水洗し、残っている塩等を除去した後、油層を70℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液10部を加え、1時間反応を行った後、洗浄水が中性になるまで水洗を行い、油層からロータリーエバポレーターを使用し、溶剤類を留去することで樹脂状のエポキシ樹脂(EP10)が得られた。得られたエポキシ樹脂(EP10)はエポキシ当量288g/eq.、関係式(α)の値は270、軟化点は69℃、溶融粘度(150℃)0.31Pa・sであった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は6376g/eq.であった。
比較例4
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに窒素ガスパージを施しながらエポキシ樹脂NC−3000−H(日本化薬株式会社製、エポキシ当量288g/eq、軟化点68℃、nの値2.5(平均値))270部、フェノールアラルキル樹脂MEH−7851SS(明和化成株式会社製、水酸基当量203g/eq、軟化点65℃)30部を仕込み、撹拌下150℃で完全に溶融させた後トリフェニルホスフィン0.40部を加え4時間反応させ、比較用のエポキシ樹脂(EP11)300部を得た。得られたエポキシ樹脂のエポキシ当量は384g/eq、関係式(α)の値は5、軟化点は94℃、溶融粘度(150℃)3.24Pa・sであった。また水酸基当量Aから算出される本エポキシ樹脂の水酸基当量は1593g/eq.であった。
試験例11〜15
得られたエポキシ樹脂EP3、EP7、EP9、EP10、および市販のNC−3000(日本化薬株式会社製、エポキシ当量270g/eq、軟化点57℃、nの値1.9(平均値))のデータを比較すると下記表7のようになる。なお保存安定性の試験結果はそれぞれメチルエチルケトンを溶剤として70重量%のエポキシ樹脂ワニスとし、5℃での冷蔵保管を行ったときの評価結果を結晶が析出する時間で示した。
TMA 熱機械測定装置:真空理工(株)製 TM−7000
昇温速度:2℃/min.
曲げ強度 :JIS K−6911
(ただし、TMAの値は、硬化時の応力のため、明確なTgを測定することが難しかったため、はじめに250℃まで5℃/min.で昇温後、冷却してから測定を行った結果である。)
Claims (10)
- 全てのRが水素原子である、請求項2に記載のエポキシ樹脂。
- 全てのArが式(3)のフェノール類である、請求項2または3に記載のエポキシ樹脂。
- 請求項1〜4のいずれか一項に記載のエポキシ樹脂及び溶剤を含有することを特徴とするエポキシ樹脂ワニス。
- 請求項1〜4のいずれか一項に記載のエポキシ樹脂及び硬化剤を含有することを特徴とする硬化性樹脂組成物。
- 請求項1〜4のいずれか一項に記載のエポキシ樹脂及びシアネート樹脂もしくはそのプレポリマーを含有することを特徴とする硬化性樹脂組成物。
- 請求項6または7に記載の硬化性樹脂組成物を硬化してなる硬化物。
- 請求項5に記載のエポキシ樹脂ワニスまたは請求項6に記載の硬化性樹脂組成物を基材に含浸させてなることを特徴とするプリプレグ。
- 請求項9に記載のプリプレグを1枚でまたは2枚以上重ね合わせ、加熱加圧してなることを特徴とする難燃性積層板または銅張積層板。
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CN (1) | CN101291972B (ja) |
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JP2008074934A (ja) * | 2006-09-20 | 2008-04-03 | Mitsubishi Gas Chem Co Inc | プリプレグの製造方法 |
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MY148660A (en) * | 2007-04-10 | 2013-05-15 | Sumitomo Bakelite Co | Resin composition, prepreg, laminated board, multilayer printed wiring board and semiconductor device |
JP5604106B2 (ja) * | 2007-08-28 | 2014-10-08 | 日本化薬株式会社 | 反応性カルボキシレート化合物、それを用いた硬化型樹脂組成物、およびその用途 |
US8318292B2 (en) * | 2008-03-26 | 2012-11-27 | Sumitomo Bakelite Co., Ltd. | Resin sheet with copper foil, multilayer printed wiring board, method for manufacturing multilayer printed wiring board and semiconductor device |
US20100028688A1 (en) * | 2008-08-01 | 2010-02-04 | Wilbert Funeral Services Inc. | Adhesive for plastic-lined concrete structure and method of producing a plastic-lined concrete structure |
KR101303681B1 (ko) | 2009-03-09 | 2013-09-04 | 파나소닉 주식회사 | 투명 필름 |
DE102009003132A1 (de) * | 2009-05-15 | 2010-11-18 | Robert Bosch Gmbh | Kunststoffformmasse sowie Verfahren zu deren Herstellung |
CN101722694A (zh) * | 2009-11-17 | 2010-06-09 | 丹阳市永和电器科技有限公司 | 一种高Tg高导热型铝基覆铜箔层压板 |
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JP6163804B2 (ja) * | 2012-03-14 | 2017-07-19 | 日立化成株式会社 | 相容化樹脂の製造法、熱硬化性樹脂組成物、プリプレグ及び積層板 |
JP5708612B2 (ja) * | 2012-10-16 | 2015-04-30 | 三菱瓦斯化学株式会社 | プリプレグの製造方法 |
CN105612190B (zh) * | 2013-10-09 | 2017-11-10 | 日本化药株式会社 | 酚树脂、环氧树脂、环氧树脂组合物、预浸料及它们的固化物 |
DE102013223490B4 (de) * | 2013-11-18 | 2023-07-06 | Robert Bosch Gmbh | Verfahren zur Herstellung einer strukturierten Oberfläche |
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JP2005015616A (ja) * | 2003-06-26 | 2005-01-20 | Kyocera Chemical Corp | 積層板用樹脂組成物、有機基材プリプレグ、金属箔張り積層板及びプリント配線板 |
JP2005206707A (ja) * | 2004-01-23 | 2005-08-04 | Sumitomo Bakelite Co Ltd | 樹脂組成物、プリプレグおよび積層板 |
JP2005248147A (ja) | 2004-02-04 | 2005-09-15 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物及びそれを用いたプリプレグ、金属張積層板、印刷配線板 |
US20080200636A1 (en) * | 2005-02-25 | 2008-08-21 | Masataka Nakanishi | Epoxy Resin, Hardenable Resin Composition Containing the Same and Use Thereof |
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TWI400264B (zh) | 2013-07-01 |
CN101291972B (zh) | 2012-04-04 |
US20090117388A1 (en) | 2009-05-07 |
CN101291972A (zh) | 2008-10-22 |
WO2007046316A1 (ja) | 2007-04-26 |
TW200728343A (en) | 2007-08-01 |
MY149580A (en) | 2013-09-13 |
US8198381B2 (en) | 2012-06-12 |
JP5199669B2 (ja) | 2013-05-15 |
KR101324535B1 (ko) | 2013-11-01 |
KR20080064167A (ko) | 2008-07-08 |
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