JP2008208315A - ノンハロゲン難燃性接着剤およびそれを用いたフレキシブルプリント配線板用材料 - Google Patents
ノンハロゲン難燃性接着剤およびそれを用いたフレキシブルプリント配線板用材料 Download PDFInfo
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- JP2008208315A JP2008208315A JP2007049126A JP2007049126A JP2008208315A JP 2008208315 A JP2008208315 A JP 2008208315A JP 2007049126 A JP2007049126 A JP 2007049126A JP 2007049126 A JP2007049126 A JP 2007049126A JP 2008208315 A JP2008208315 A JP 2008208315A
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- Prior art keywords
- general formula
- flame retardant
- phosphorus
- formula
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- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 70
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 69
- 239000003063 flame retardant Substances 0.000 title claims abstract description 33
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title claims description 25
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 56
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 56
- 239000011574 phosphorus Substances 0.000 claims abstract description 56
- 239000013034 phenoxy resin Substances 0.000 claims abstract description 30
- 229920006287 phenoxy resin Polymers 0.000 claims abstract description 30
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 239000003822 epoxy resin Substances 0.000 claims abstract description 24
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000005227 gel permeation chromatography Methods 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
- 229910000679 solder Inorganic materials 0.000 abstract description 5
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 150000002366 halogen compounds Chemical class 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 19
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000001723 curing Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 239000012790 adhesive layer Substances 0.000 description 11
- 229920001721 polyimide Polymers 0.000 description 10
- 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 9
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 239000011889 copper foil Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000011417 postcuring Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000007747 plating Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 0 Cc1c(*)c(*)c(*c2c(*)c(*)c(C)c(I)c2*)c(*)c1* Chemical compound Cc1c(*)c(*)c(*c2c(*)c(*)c(C)c(I)c2*)c(*)c1* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000007731 hot pressing Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- -1 2,5-dihydroxyphenyl Chemical group 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 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
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 210000001787 dendrite Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 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 1
- 238000013007 heat curing Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Production Of Multi-Layered Print Wiring Board (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Polyethers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007049126A JP2008208315A (ja) | 2007-02-28 | 2007-02-28 | ノンハロゲン難燃性接着剤およびそれを用いたフレキシブルプリント配線板用材料 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007049126A JP2008208315A (ja) | 2007-02-28 | 2007-02-28 | ノンハロゲン難燃性接着剤およびそれを用いたフレキシブルプリント配線板用材料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008208315A true JP2008208315A (ja) | 2008-09-11 |
| JP2008208315A5 JP2008208315A5 (enExample) | 2010-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007049126A Pending JP2008208315A (ja) | 2007-02-28 | 2007-02-28 | ノンハロゲン難燃性接着剤およびそれを用いたフレキシブルプリント配線板用材料 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2008208315A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011153706A (ja) * | 2009-12-28 | 2011-08-11 | Nitto Denko Corp | ガスケット |
| JP2020125471A (ja) * | 2019-02-06 | 2020-08-20 | 日鉄ケミカル＆マテリアル株式会社 | フェノキシ樹脂及びその製造方法、その樹脂組成物並びに硬化物 |
| JP2021050267A (ja) * | 2019-09-24 | 2021-04-01 | 日鉄ケミカル＆マテリアル株式会社 | フェノキシ樹脂の製造方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001310939A (ja) * | 2000-04-27 | 2001-11-06 | Toto Kasei Co Ltd | 熱可塑性ポリヒドロキシポリエーテル樹脂及びそれから成形した絶縁性フィルム |
| JP2002003711A (ja) * | 2000-06-21 | 2002-01-09 | Toto Kasei Co Ltd | 熱可塑性ポリヒドロキシポリエーテル樹脂を含有する硬化性樹脂組成物 |
| JP2003176470A (ja) * | 2001-12-12 | 2003-06-24 | Tokai Rubber Ind Ltd | フレキシブル印刷配線板用難燃性接着剤組成物およびそれを用いたフレキシブル印刷配線板 |
| JP2003286391A (ja) * | 2002-03-28 | 2003-10-10 | Nippon Steel Chem Co Ltd | エポキシ樹脂組成物、ワニス、このエポキシ樹脂組成物を用いたフィルム状接着剤及びその硬化物 |
| JP2005272567A (ja) * | 2004-03-24 | 2005-10-06 | Toray Ind Inc | 半導体装置用接着剤組成物およびそれを用いたカバーレイフィルム、接着剤シート、銅張りポリイミドフィルム |
| JP2005290229A (ja) * | 2004-03-31 | 2005-10-20 | Arisawa Mfg Co Ltd | 難燃性樹脂組成物及び当該難燃性樹脂組成物を用いたフレキシブルプリント配線板用金属張積層板 |
| JP2007002110A (ja) * | 2005-06-24 | 2007-01-11 | Sumitomo Bakelite Co Ltd | 半導体封止用樹脂組成物および半導体装置 |
-
2007
- 2007-02-28 JP JP2007049126A patent/JP2008208315A/ja active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001310939A (ja) * | 2000-04-27 | 2001-11-06 | Toto Kasei Co Ltd | 熱可塑性ポリヒドロキシポリエーテル樹脂及びそれから成形した絶縁性フィルム |
| JP2002003711A (ja) * | 2000-06-21 | 2002-01-09 | Toto Kasei Co Ltd | 熱可塑性ポリヒドロキシポリエーテル樹脂を含有する硬化性樹脂組成物 |
| JP2003176470A (ja) * | 2001-12-12 | 2003-06-24 | Tokai Rubber Ind Ltd | フレキシブル印刷配線板用難燃性接着剤組成物およびそれを用いたフレキシブル印刷配線板 |
| JP2003286391A (ja) * | 2002-03-28 | 2003-10-10 | Nippon Steel Chem Co Ltd | エポキシ樹脂組成物、ワニス、このエポキシ樹脂組成物を用いたフィルム状接着剤及びその硬化物 |
| JP2005272567A (ja) * | 2004-03-24 | 2005-10-06 | Toray Ind Inc | 半導体装置用接着剤組成物およびそれを用いたカバーレイフィルム、接着剤シート、銅張りポリイミドフィルム |
| JP2005290229A (ja) * | 2004-03-31 | 2005-10-20 | Arisawa Mfg Co Ltd | 難燃性樹脂組成物及び当該難燃性樹脂組成物を用いたフレキシブルプリント配線板用金属張積層板 |
| JP2007002110A (ja) * | 2005-06-24 | 2007-01-11 | Sumitomo Bakelite Co Ltd | 半導体封止用樹脂組成物および半導体装置 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011153706A (ja) * | 2009-12-28 | 2011-08-11 | Nitto Denko Corp | ガスケット |
| JP2020125471A (ja) * | 2019-02-06 | 2020-08-20 | 日鉄ケミカル＆マテリアル株式会社 | フェノキシ樹脂及びその製造方法、その樹脂組成物並びに硬化物 |
| JP2021050267A (ja) * | 2019-09-24 | 2021-04-01 | 日鉄ケミカル＆マテリアル株式会社 | フェノキシ樹脂の製造方法 |
| JP7412939B2 (ja) | 2019-09-24 | 2024-01-15 | 日鉄ケミカル＆マテリアル株式会社 | フェノキシ樹脂の製造方法 |
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