JP6943738B2 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JP6943738B2 JP6943738B2 JP2017224020A JP2017224020A JP6943738B2 JP 6943738 B2 JP6943738 B2 JP 6943738B2 JP 2017224020 A JP2017224020 A JP 2017224020A JP 2017224020 A JP2017224020 A JP 2017224020A JP 6943738 B2 JP6943738 B2 JP 6943738B2
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- 239000011342 resin composition Substances 0.000 title claims description 53
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- 239000011347 resin Substances 0.000 claims description 48
- 229910052698 phosphorus Inorganic materials 0.000 claims description 47
- 239000011574 phosphorus Substances 0.000 claims description 45
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- 229920001955 polyphenylene ether Polymers 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
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- 229920000877 Melamine resin Polymers 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229920000388 Polyphosphate Polymers 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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- 150000002170 ethers Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
- 150000002366 halogen compounds Chemical class 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
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- 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 4
- 150000002989 phenols Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 239000001205 polyphosphate Substances 0.000 description 4
- 235000011176 polyphosphates Nutrition 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 229910021538 borax Inorganic materials 0.000 description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 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 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 2
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- 125000005647 linker group Chemical group 0.000 description 2
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- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- LOZAIRWAADCOHQ-UHFFFAOYSA-N triphosphazene Chemical compound PNP=NP LOZAIRWAADCOHQ-UHFFFAOYSA-N 0.000 description 1
- MHEGXVLDEDJADA-UHFFFAOYSA-N tris(2,3,4-trimethylphenyl) phosphate Chemical compound CC1=C(C)C(C)=CC=C1OP(=O)(OC=1C(=C(C)C(C)=CC=1)C)OC1=CC=C(C)C(C)=C1C MHEGXVLDEDJADA-UHFFFAOYSA-N 0.000 description 1
- LRSNDFOWYYKLHB-UHFFFAOYSA-N tris(2,3-dibromophenyl) phosphate Chemical compound BrC1=CC=CC(OP(=O)(OC=2C(=C(Br)C=CC=2)Br)OC=2C(=C(Br)C=CC=2)Br)=C1Br LRSNDFOWYYKLHB-UHFFFAOYSA-N 0.000 description 1
- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- YSENUEFXTYTOBY-UHFFFAOYSA-N tris(3-bromo-2-chlorophenyl) phosphate Chemical compound C1=CC(=C(C(=C1)Br)Cl)OP(=O)(OC2=C(C(=CC=C2)Br)Cl)OC3=C(C(=CC=C3)Br)Cl YSENUEFXTYTOBY-UHFFFAOYSA-N 0.000 description 1
- LKOCAGKMEUHYBV-UHFFFAOYSA-N tris(3-bromo-3-chloropropyl) phosphate Chemical compound ClC(Br)CCOP(=O)(OCCC(Cl)Br)OCCC(Cl)Br LKOCAGKMEUHYBV-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
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Description
即ち、本発明は、(A)ポリフェニレンエーテル樹脂及び(E)下記式(1)で表される含リン化合物を含有してなる樹脂組成物を提供するものである。
R21〜R24で表されるアルケニル基としては、例えば、ビニル基、アリル基などの基が挙げられる。
R21〜R24で表されるアルキニル基としては、例えば、エチニル、2−プロピニルなどの基が挙げられる。
R21〜R24で表されるアルキルカルボニル基としては、例えばアセチル基などの基が挙げられる。
R21〜R24で表されるアルケニルカルボニル基としては、例えば、アクリロイル基、メタクリロイル基を挙げることができる。
ポリフェニレンエーテル樹脂の中でも、一般式(II)中、R21〜R24がそれぞれ独立して、水素原子、又はアルキル基であるものがコスト、入手が容易である点で特に好ましい。
R12で表される酸素及び硫黄から選ばれる原子を含んでいる場合がある炭化水素基としては、炭素数1〜6のアルキレン基のほか、−S−、−SO−、−SO2−が挙げられる。
式(6−3)〜(6−5)におけるa、b、cは、それぞれ独立して、1〜5の整数を表す;
式(6−6)及び(6−7)におけるd、eは、それぞれ独立して、1〜10の整数を表す;
式(6−8)におけるhは、1〜50の整数を表し、式(6−11)におけるAは水素原子、又は−OR17を表し、R17は炭素数1〜6のアルキル基を表す。
また、硬化剤として潜在性硬化剤を選択した場合には、エポキシ樹脂及び潜在性硬化剤の合計量に対し、0.1〜80質量%、好ましくは0.5〜60質量%、さらに好ましくは1〜40質量%である。
尚、以下の実施例等における%は、特に記載がない限り質量基準である。
固形分濃度が約70質量%となるように、NORYL SA−90(SABIC社製;低分子量ポリフェニレンエーテル樹脂)60質量部、トリアリルイソシアヌレート(TAIC)40質量部、パーブチルP(日本油脂(株)製;ラジカル発生剤)1.0質量部及び下記含リン化合物P−1 29質量部をトルエンに投入し、90℃で、完全に溶解するまで撹拌して樹脂溶液状の樹脂組成物を作製した。
次に、得られた樹脂組成物を130℃、2時間の条件で加熱乾燥させた後、220℃、4時間の条件で加熱することで樹脂組成物の硬化物を作製した。
含リン化合物P−1を下記含リン化合物P−2 24質量部に変更した以外は実施例1と同様にして樹脂組成物及びその硬化物を作製し、実施例1と同様の評価を行った。
含リン化合物P−1を下記含リン化合物P−3 28質量部に変更した以外は実施例1と同様にして樹脂組成物及びその硬化物を作製し、実施例1と同様の評価を行った。
含リン化合物P−1を下記含リン化合物P−4 27質量部に変更した以外は実施例1と同様にして樹脂組成物及びその硬化物を作製し、実施例1と同様の評価を行った。
含リン化合物P−1を下記含リン化合物P−5 25質量部に変更した以外は実施例1と同様にして樹脂組成物及びその硬化物を作製し、実施例1と同様の評価を行った。
含リン化合物P−1を下記含リン化合物P−6 25質量部に変更した以外は実施例1と同様にして樹脂組成物及びその硬化物を作製し、実施例1と同様の評価を行った。
含リン化合物P−1を使用しない以外は実施例1と同様に樹脂組成物及びその硬化物を作製し、実施例1と同様の評価を行った。
含リン化合物P−1を下記含リン化合物HP−1 42質量部に変更した以外は実施例1と同様にして樹脂組成物及びその硬化物を作製し、実施例1と同様の評価を行った。
Claims (12)
- 式(1)中、R1及びR2がそれぞれ独立して、アルキル基である、請求項1に記載の樹脂組成物。
- 式(1)中、R1及びR2が共に−NR4R5である、請求項1に記載の樹脂組成物。
- 式(1)中、X及びYが共に酸素原子である、請求項1〜3の何れか1項に記載の樹脂組成物。
- 式(1)中、R3が、芳香環を少なくとも1個有する炭化水素基である、請求項1〜4の何れか1項に記載の樹脂組成物。
- 式(1)中、R3が、下記一般式(2−1)、(2−2)、(2−4)、(2−5)、及び(2−6)から選択される何れかの構造を有する基である、請求項5に記載の樹脂組成物。
- (A)成分であるポリフェニレンエーテル樹脂が、末端に水酸基を有するポリフェニレンエーテル樹脂である、請求項1〜6の何れか1項に記載の樹脂組成物。
- (A)成分であるポリフェニレンエーテル樹脂が、末端にエチレン性二重結合を有する変性ポリフェニレンエーテル樹脂である、請求項1〜6の何れか1項に記載の樹脂組成物。
- (B)エポキシ基及び/又はイソシアネート基と、エチレン性二重結合基とを有する化合物を含有する、請求項1〜8の何れか1項に記載の樹脂組成物。
- (C)エチレン性二重結合基を分子中に2個以上有する架橋型硬化剤を含有する、請求項1〜9の何れか1項に記載の樹脂組成物。
- (D)ラジカル開始剤を含有する、請求項1〜10の何れか1項に記載の樹脂組成物。
- 請求項1〜11の何れか1項に記載の樹脂組成物の硬化物を有する積層板。
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