WO2015188377A1 - 一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 - Google Patents
一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 Download PDFInfo
- Publication number
- WO2015188377A1 WO2015188377A1 PCT/CN2014/079854 CN2014079854W WO2015188377A1 WO 2015188377 A1 WO2015188377 A1 WO 2015188377A1 CN 2014079854 W CN2014079854 W CN 2014079854W WO 2015188377 A1 WO2015188377 A1 WO 2015188377A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- parts
- weight
- halogen
- free
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 33
- UADBQCGSEHKIBH-UHFFFAOYSA-N 3-phenoxy-2,4-dihydro-1h-1,3,5,2,4,6-triazatriphosphinine Chemical compound P1N=PNPN1OC1=CC=CC=C1 UADBQCGSEHKIBH-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000011342 resin composition Substances 0.000 title claims abstract description 21
- 229920005989 resin Polymers 0.000 claims abstract description 82
- 239000011347 resin Substances 0.000 claims abstract description 82
- 239000003822 epoxy resin Substances 0.000 claims abstract description 47
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 47
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 239000011256 inorganic filler Substances 0.000 claims abstract description 9
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 60
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims description 29
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 25
- 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 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 21
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- -1 phenol compound Chemical class 0.000 claims description 12
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 229920001955 polyphenylene ether Polymers 0.000 claims description 9
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 8
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl 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
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 5
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 5
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 4
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical group CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 239000000378 calcium silicate Substances 0.000 claims description 4
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 4
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 4
- 229910052570 clay Inorganic materials 0.000 claims description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 4
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
- 239000000347 magnesium hydroxide Substances 0.000 claims description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 4
- 239000000395 magnesium oxide Substances 0.000 claims description 4
- 239000010445 mica Substances 0.000 claims description 4
- 229910052618 mica group Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 229910052623 talc Inorganic materials 0.000 claims description 4
- 239000010456 wollastonite Substances 0.000 claims description 4
- 229910052882 wollastonite Inorganic materials 0.000 claims description 4
- 239000010457 zeolite Substances 0.000 claims description 4
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical group [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
- QOVWSDOHZFBJSO-UHFFFAOYSA-N C=CC=C.C=CC=CC1=CC=CC=C1 Chemical compound C=CC=C.C=CC=CC1=CC=CC=C1 QOVWSDOHZFBJSO-UHFFFAOYSA-N 0.000 claims description 2
- HSCPDMJPJJSHDA-UHFFFAOYSA-N benzylbenzene;pyrrole-2,5-dione Chemical class O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.C=1C=CC=CC=1CC1=CC=CC=C1 HSCPDMJPJJSHDA-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 239000012779 reinforcing material Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 11
- 239000003063 flame retardant Substances 0.000 abstract description 8
- 239000000758 substrate Substances 0.000 abstract description 6
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000003292 glue Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011889 copper foil Substances 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 238000004080 punching Methods 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- NFPBWZOKGZKYRE-UHFFFAOYSA-N 2-propan-2-ylperoxypropane Chemical compound CC(C)OOC(C)C NFPBWZOKGZKYRE-UHFFFAOYSA-N 0.000 description 2
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 2
- 241000519995 Stachys sylvatica Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004643 cyanate ester Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001622 bismuth compounds Chemical class 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000009774 resonance method Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LOZAIRWAADCOHQ-UHFFFAOYSA-N triphosphazene Chemical compound PNP=NP LOZAIRWAADCOHQ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/08—Epoxidised polymerised polyenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2363/08—Epoxidised polymerised polyenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2435/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
- C08J2435/06—Copolymers with vinyl aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2463/08—Epoxidised polymerised polyenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/22—Halogen free composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0104—Properties and characteristics in general
- H05K2201/012—Flame-retardant; Preventing of inflammation
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0137—Materials
- H05K2201/0145—Polyester, e.g. polyethylene terephthalate [PET], polyethylene naphthalate [PEN]
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0203—Fillers and particles
- H05K2201/0206—Materials
- H05K2201/0209—Inorganic, non-metallic particles
Definitions
- the present invention relates to a phenoxycyclotriphosphazene active ester, a resin-free composition for use in the preparation of a prepreg, a laminate, and a printed wiring board, and a use thereof.
- a printed wiring board is developed toward a higher-order multilayer printed wiring board while being more precisely wired.
- an effective method is to lower the dielectric constant of the material used.
- an effective method is to use a material having a lower dielectric loss tangent (dielectric loss).
- one of the objects of the present invention is to provide a phenoxycyclotriphosphazene activity.
- the ester is introduced into the thermosetting resin, and the reactive group carried by it reacts with a specific thermosetting resin or the like without generating a hydroxyl group, which satisfies the halogen-free flame retardant requirement and does not change the dielectric constant and dielectric loss.
- the corner tangent improves the electrical performance, making it possible to halogen-free high-frequency high-speed substrate materials.
- the at least 65% is, for example, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%,
- n is, for example, 0.28, 0.35, 0.42, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2.
- An exemplary method for preparing an active ester of phenoxycyclotriphosphazene is as follows:
- the solvent, the hydroxy-containing phenoxycyclotriphosphazene (the molar ratio of the two hydroxyl groups is more than 65%), the acid binding agent and the catalyst are added to the reaction device, stirred, and protected by nitrogen gas, less than 20 ° C A certain amount of p-benzoyl chloride is gradually added dropwise. After reacting for 1 to 8 hours, an excess of phenol is added, the reaction is continued for 1 to 8 hours, cooled to room temperature, suction filtered, and the filtrate is subjected to pressure distillation to evaporate the solvent to obtain a viscous product. , that is, phenoxycyclotriphosphazene active ester.
- the phenoxycyclotriphosphazene active ester prepared by this method is a mixture which inevitably contains other components such as impurities, wherein it contains at least 65% of the substance having the above structural formula.
- Another object of the present invention is to provide a halogen-free resin composition
- a halogen-free resin composition comprising, by weight: by weight:
- thermosetting resin is selected from any one or at least two of an epoxy resin, a benzoxazine resin, a cyanate resin, a bismaleimide resin, a reactive polyphenylene ether resin or a hydrocarbon resin. mixture.
- the reactive polyphenylene ether resin is a polyphenylene ether resin which is crosslinked with a reactive group in the main chain.
- the parts by weight of the phenoxycyclotriphosphazene active ester are, for example, 7 parts by weight, 9 parts by weight, 11 parts by weight, 13 parts by weight, 15 parts by weight, 17 parts by weight, 19 parts by weight, 21 parts by weight, 23 Parts by weight, 25 parts by weight, 27 parts by weight, 29 parts by weight, 31 parts by weight, 35 parts by weight, 37 parts by weight, 39 parts by weight, 41 parts by weight, 43 parts by weight, 45 parts by weight, 47 parts by weight or 49 parts by weight .
- the parts by weight of the thermosetting resin are, for example, 18 parts by weight, 21 parts by weight, 24 parts by weight, 27 parts by weight, 30 parts by weight, 33 parts by weight, 36 parts by weight, 39 parts by weight, 42 parts by weight, 45 parts by weight, 48 parts by weight, 51 parts by weight, 54 parts by weight, 57 parts by weight, 60 parts by weight, 63 parts by weight, 66 parts by weight, 69 parts by weight, 72 parts by weight, 75 parts by weight, 78 parts by weight, 81 parts by weight or 84% by weight Share.
- the parts by weight of the curing agent are, for example, 2 parts by weight, 4 parts by weight, 6 parts by weight, 8 parts by weight, 10 parts by weight, 12 parts by weight, 14 parts by weight, 16 parts by weight, 18 parts by weight, 20 parts by weight, 22 parts by weight, 24 parts by weight, 26 parts by weight, 28 parts by weight, 30 parts by weight, 32 parts by weight or 34 parts by weight.
- the part by weight of the curing accelerator is, for example, 0.2 parts by weight, 0.5 parts by weight, 0.8 parts by weight, 1.1 parts by weight, 1.4 parts by weight, 1.7 parts by weight, 2 parts by weight, 2.3 parts by weight, 2.6 parts by weight, 2.9 parts by weight, 3.2 parts by weight, 3.5 parts by weight, 3.8 parts by weight, 4.1 parts by weight, 4.4 parts by weight, 4.6 parts by weight Parts or 4.8 parts by weight.
- the parts by weight of the inorganic filler are, for example, 4 parts by weight, 8 parts by weight, 12 parts by weight, 16 parts by weight, 20 parts by weight, 24 parts by weight, 28 parts by weight, 32 parts by weight, 36 parts by weight, 40 parts by weight, 44 parts by weight, 48 parts by weight, 52 parts by weight, 56 parts by weight, 60 parts by weight, 64 parts by weight, 68 parts by weight, 72 parts by weight, 76 parts by weight, 80 parts by weight, 84 parts by weight, 88 parts by weight, 92 parts by weight Parts, 96 parts by weight or 98 parts by weight, preferably 25 to 100 parts by weight.
- the invention introduces phenoxycyclotriphosphazene active ester into the thermosetting resin, and reacts the active ester with the epoxy resin to generate no hydroxyl group, thereby satisfying the halogen-free flame retardant requirement and improving the electrical properties of the system (reducing and stabilizing) Dk and Df) make it possible to halogen-free high-frequency high-speed substrate materials.
- the thermosetting resin has a dicyclopentadiene, a biphenyl or a naphthalene ring, and its dielectric properties are superior to those of other structures of thermosetting resins because of its containing dicyclopentadiene, biphenyl or naphthalene ring groups.
- the epoxy resin is selected from the group consisting of bisphenol A epoxy resin, bisphenol F epoxy resin, DCPD epoxy resin, trisphenol epoxy resin, biphenyl epoxy resin or naphthol epoxy resin. Any one or a mixture of at least two.
- the mixture is, for example, a mixture of a bisphenol A type epoxy resin and a bisphenol F type epoxy resin, a mixture of a DCPD epoxy resin and a trisphenol epoxy resin, a mixture of a biphenyl epoxy resin and a naphthol epoxy resin, A mixture of a phenolic A type epoxy resin, a bisphenol F type epoxy resin and a DCPD epoxy resin, a mixture of a trisphenol epoxy resin, a biphenyl epoxy resin, and a naphthol epoxy resin.
- the epoxy resin has a phosphorus content of 1.5-6.0 wt% (for example, 1.8 wt%, 2.1 wt%, 2.4 wt%, 2.7 wt%, 3 wt%, 3.3 wt%, 3.6 wt%, 3.9 wt%). , 4.2 wt%, 4.5 wt%, 4.8 wt%, 5.1 wt%, 5.4 wt% or 5.7 wt%) of phosphorus-containing epoxy resin.
- the benzoxazine resin is selected from the group consisting of bisphenol A type benzoxazine resin, bisphenol F type benzoxazole Any one or a mixture of at least two of a azine resin, a DCPD type benzoxazine resin or a phenolphthalein type benzoxazine resin.
- the mixture is, for example, a mixture of a bisphenol A type benzoxazine resin and a bisphenol F type benzoxazine resin, a mixture of a DCPD type benzoxazine resin and a phenolphthalein type benzoxazine resin, and a bisphenol A type benzoate.
- the cyanate resin is selected from any one or a mixture of at least two of a bisphenol A type cyanate resin, a DCPD type cyanate resin or a phenol type cyanate resin.
- the mixture is, for example, a mixture of a bisphenol A type cyanate resin and a DCPD type cyanate resin, a mixture of a phenolic type cyanate resin and a bisphenol A type cyanate resin, a DCPD type cyanate resin and a novolac type cyanide.
- the bismaleimide resin comprises 4,4'-diphenylmethane bismaleimide or / and allyl-modified diphenylmethane bismaleimide.
- the reactive polyphenylene ether resin has a number average molecular weight of from 1,000 to 7,000 and a reactive group of a hydroxyl group or a/double bond.
- the hydrocarbon resin is selected from a vinyl styrene-butadiene resin having a number average molecular weight of 11,000 or less, a vinyl polybutadiene resin having a polar group, or a maleic anhydride grafted butadiene and a styrene resin. Any one or at least two copolymers.
- the curing agent is selected from any one or a mixture of at least two of dicyandiamide, an aromatic amine, an acid anhydride, a phenolic compound, a triallylene isocyanurate or a phosphorus-containing phenolic aldehyde.
- the mixture is, for example, a mixture of dicyandiamide and an aromatic amine, a mixture of an acid anhydride and a phenolic compound, a mixture of a trienyl isocyanurate and a phosphorus-containing phenolic aldehyde, a mixture of dicyandiamide, an aromatic amine and an acid anhydride, a phenolic compound, and a different Trienyl cyanurate And a mixture of phosphorus-containing phenolic aldehydes.
- the curing accelerator is selected from the group consisting of 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, pyridine, DMP-30, hexamethylenetetramine, diisopropyl peroxide Any one of benzene, tert-butyl peroxybenzoate, 2,5-di(2-ethylhexanoylperoxy)-2,5-dimethylhexane, acetylacetonate or zincate or a mixture of at least two.
- the mixture is, for example, a mixture of 2-methylimidazole and 2-ethyl-4-methylimidazole, a mixture of 2-phenylimidazole and pyridine, a mixture of DMP-30 and hexamethylenetetramine, diisopropyl peroxide a mixture of benzene and tert-butyl peroxybenzoate, a mixture of 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethylhexane, acetylacetonate and zincate, 2 a mixture of methylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole, a mixture of pyridine, DMP-30 and hexamethylenetetramine, dicumyl peroxide, benzoic acid benzoate Mixture of butyl ester, 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethylhexane
- the inorganic filler is selected from any one or at least two of aluminum hydroxide, magnesium hydroxide, zeolite, wollastonite, silica, magnesia, calcium silicate, calcium carbonate, clay, talc or mica.
- aluminum hydroxide magnesium hydroxide
- zeolite zeolite
- wollastonite silica
- magnesia calcium silicate
- calcium carbonate clay
- talc talc or mica
- the mixture for example a mixture of aluminum hydroxide and magnesium hydroxide, a mixture of zeolite and wollastonite, a mixture of silica and magnesia, a mixture of calcium silicate and calcium carbonate, a mixture of clay, talc and mica, hydroxide A mixture of aluminum, magnesium hydroxide and zeolite, a mixture of wollastonite, silica, magnesia and calcium silicate, a mixture of calcium carbonate, clay, talc and mica.
- the term “comprising” as used in the present invention means that it may include other components in addition to the components, and these other components impart different characteristics to the halogen-free resin composition.
- the "including” of the present invention may be replaced by a closed “for” or “consisting of”.
- the halogen-free resin composition may further contain various additives, and specific examples thereof include an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a colorant, a lubricant, and the like. These various additives may be used singly or in combination of two or more kinds.
- a third object of the present invention is to provide a prepreg comprising a reinforcing material and a resin composition as described above adhered thereto by dipping and drying.
- a fourth object of the present invention is to provide a laminate comprising at least one prepreg as described above.
- a fifth object of the present invention is to provide a printed wiring board comprising at least one prepreg as described above.
- An exemplary method of preparing a laminate includes the following steps:
- the prepreg is cut into suitable sizes, neatly superimposed, and a piece of copper foil is placed on the upper and lower sides and placed in a vacuum hot press for pressing to obtain a copper clad laminate.
- the baking temperature of the step (2) is set according to the boiling point of the solvent used for the glue, the temperature is generally 85 to 175 ° C, and the baking time is generally 5 to 20 minutes.
- the pressing process adopts a stepwise pressing (step heating and boosting) method, and the specific steps are as follows: 15 minutes from room temperature to 150 ° C for 30 min, then 5 min to 180 ° C for 2 hr, and finally 30min cooling room temperature; pressure Imin from zero to 0.6MPa for 20min, then Imin rose to l.OMPa holding pressure 2.5hr; post-treatment conditions of 200 ⁇ 245 °C for l ⁇ 5hr.
- the present invention has the following beneficial effects:
- the invention introduces phenoxycyclotriphosphazene active ester into the thermosetting resin, and reacts the active ester with the epoxy resin to generate no hydroxyl group, thereby satisfying the halogen-free flame retardant requirement and improving the electrical performance of the system.
- Low, stable Dk and Df) make it possible to halogen-free high-frequency high-speed substrate materials.
- an active ester of phenoxycyclotriphosphazene and an epoxy resin a benzoxazine resin, a cyanate resin, a bismaleimide resin, a small molecule polyphenylene ether resin, a hydrocarbon resin It is compounded with thermosetting resin, cured with a composite curing agent, mixed with some organic and inorganic fillers, glued, laminated, and laminated to obtain a copper clad laminate.
- the obtained copper clad laminate meets halogen-free requirements, excellent heat resistance and moisture resistance, and dielectric loss. Low advantage.
- the solvent, the hydroxy-containing phenoxycyclotriphosphazene (the ratio of the two hydroxyl groups is more than 65%), the acid binding agent and the catalyst are added to the reaction device, stirred, and protected by nitrogen gas, and a certain amount is gradually added at a low temperature.
- an appropriate amount of phenol is added, the reaction is continued for 1 to 8 hours, cooled to room temperature, suction filtered, and the filtrate is subjected to pressure distillation, and the solvent is evaporated to give a viscous product.
- DCPD epoxy resin selected DCPD epoxy resin was HP-7200H (DIC), equivalent 275-280), an appropriate amount of imidazole and pyridine were added, and the mixture was stirred and mixed to obtain a gum solution.
- a 300 X 300 cm, smooth, flat E-glass cloth was applied, and the above glue was uniformly applied and baked in an oven at 155 ° C for 7 min to obtain a bonded sheet.
- Stepwise (step-by-step heating and boosting) program is used, in which 15 minutes from room temperature to 150 ° C for 30 min, then 5 min to 180 ° C for 2 hr, last 30 min to cool room temperature; pressure Imin rises from zero to The pressure was maintained at 0.6 MPa for 20 min, and then Imin was raised to 1.0 MPa for 2.5 hr.
- the basic performance is shown in Table 1.
- the solvent, the hydroxy-containing phenoxycyclotriphosphazene (the ratio of the two hydroxyl groups is more than 65%), the acid binding agent and the catalyst are added to the reaction device, stirred, and protected by nitrogen gas, and a certain amount is gradually added at a low temperature.
- an appropriate amount of phenol is added, the reaction is continued for 1 to 8 hours, cooled to room temperature, suction filtered, and the filtrate is subjected to pressure distillation, and the solvent is evaporated to give a viscous product.
- DCPD benzoxazine 40 g selected DCPD benzoxazine is LZ8260 (Huntsman)
- DCPD epoxy resin 20 g selected DCPD epoxy resin is HP-7200H (DIC) ), equivalent 275-280
- styrene/maleic anhydride 10g selected anhydride is EF-30, Sartomer
- appropriate amount of imidazole and pyridine stirred and mixed to obtain a glue.
- a 300 X 300 cm, smooth, flat E-glass cloth was applied, and the above glue was uniformly applied and baked in an oven at 155 ° C for 7 min to obtain a bonded sheet.
- Stepwise (step-by-step heating and boosting) program suppression in which 15 minutes from room temperature to 150 ° C for 30 min, then 5 min to 190 ° C for 2 hr, the last 30 min to cool room temperature; pressure Imin rose from zero to The pressure was maintained at 0.6 MPa for 20 min, and then Imin was raised to 1.0 MPa for 2.5 hr.
- the basic performance is shown in Table 1.
- the solvent, the hydroxy-containing phenoxycyclotriphosphazene (the ratio of the two hydroxyl groups is more than 65%), the acid binding agent and the catalyst are added to the reaction device, stirred, and protected by nitrogen gas, and a certain amount is gradually added at a low temperature.
- an appropriate amount of phenol is added, the reaction is continued for 1 to 8 hours, cooled to room temperature, suction filtered, and the filtrate is subjected to pressure distillation, and the solvent is evaporated to give a viscous product.
- a 300 X 300 cm, smooth, flat E-glass cloth was applied, and the above glue was uniformly applied and baked in an oven at 155 ° C for 7 min to obtain a bonded sheet.
- Step-by-step (step-by-step heating and boosting) program suppression in which 15 minutes from room temperature to 150 ° C for 30 min, then 5 min to 210 ° C for 2 hr, the last 30 min to cool the room temperature; pressure Imin rose from zero to The pressure was maintained at 0.6 MPa for 20 min, and then Imin was raised to 1.0 MPa for 2.5 hr.
- Table 1 The basic performance is shown in Table 1.
- the solvent, the hydroxy-containing phenoxycyclotriphosphazene (the ratio of the two hydroxyl groups is more than 65%), the acid binding agent and the catalyst are added to the reaction device, stirred, and protected by nitrogen gas, and a certain amount is gradually added at a low temperature.
- an appropriate amount of phenol is added, the reaction is continued for 1 to 8 hours, cooled to room temperature, suction filtered, and the filtrate is subjected to pressure distillation, and the solvent is evaporated to give a viscous product.
- a 300 X 300 cm, smooth, flat E-glass cloth was applied, and the above glue was uniformly applied and baked in an oven at 155 ° C for 7 min to obtain a bonded sheet.
- the solvent, the hydroxy-containing phenoxycyclotriphosphazene (the ratio of the two hydroxyl groups is more than 65%), the acid binding agent and the catalyst are added to the reaction device, stirred, and protected by nitrogen gas, and a certain amount is gradually added at a low temperature.
- an appropriate amount of phenol is added, the reaction is continued for 1 to 8 hours, cooled to room temperature, suction filtered, and the filtrate is subjected to pressure distillation, and the solvent is evaporated to give a viscous product.
- cyanate ester selected cyanate ester is LONZA-Primaset BA-230s
- naphthol epoxy resin 5 g HPC-9500 (DIC)
- appropriate amount of aluminum acetylacetonate is added.
- pyridine stirring and mixing to obtain a glue.
- a 300 X 300 cm, smooth, flat E-glass cloth was applied, and the above glue was uniformly applied and baked in an oven at 155 ° C for 7 min to obtain a bonded sheet.
- Step-by-step (step-by-step heating and boosting) program suppression in which 15 minutes from room temperature to 150 ° C for 30 min, then 5 min to 210 ° C for 2 hr, the last 30 min to cool the room temperature; pressure Imin rose from zero to The pressure was maintained at 0.6 MPa for 20 min, and then Imin was raised to 1.0 MPa for 2.5 hr.
- Table 1 The basic performance is shown in Table 1.
- the solvent, the hydroxy-containing phenoxycyclotriphosphazene (the ratio of which contains 2 hydroxyl groups is more than 65%), the acid binding agent and the catalyst are added to the reaction device, stirred, and protected by nitrogen gas, and gradually added at a low temperature.
- the amount of p-benzoyl chloride is adjusted, and after reacting for 1 to 8 hours, an appropriate amount of phenol is added, the reaction is continued for 1 to 8 hours, cooled to room temperature, suction filtered, and the filtrate is subjected to pressure distillation to evaporate the solvent to obtain a viscous product.
- DCPD epoxy resin selected DCPD epoxy resin was HP-7200H (DIC), equivalent 275-280), an appropriate amount of imidazole and pyridine were added, and the mixture was stirred and mixed to obtain a gum solution.
- a 300 X 300 cm, smooth, flat E-glass cloth was applied, and the above glue was uniformly applied and baked in an oven at 155 ° C for 7 min to obtain a bonded sheet.
- a piece of bonded embossed sheet was superposed, and 18 ⁇ of copper foil was attached to the upper and lower sides, and pressed in a vacuum hot press to obtain a copper clad laminate.
- Stepwise (step-by-step heating and boosting) program is used, in which 15 minutes from room temperature to 150 ° C for 30 min, then 5 min to 180 ° C for 2 hr, last 30 min to cool room temperature; pressure Imin rises from zero to The pressure was maintained at 0.6 MPa for 20 min, and then Imin was raised to 1.0 MPa for 2.5 hr.
- the basic performance is shown in Table 1.
- Example 3 30 g of the phenoxycyclotriphosphazene active ester in Example 3 was replaced with 30 g of the phosphorus-containing phenolic aldehyde (the selected phosphorus-containing phenolic aldehyde was Dow Chemical XZ92741), and the remainder remained unchanged.
- Example 4 30 g of the phenoxycyclotriphosphazene active ester in Example 4 was replaced with 30 g of the phosphorus-containing phenolic aldehyde (the selected phosphorus-containing phenolic aldehyde was Dow Chemical XZ92741), and the rest remained unchanged.
- Example 1 30 g of the phenoxycyclotriphosphazene active ester in Example 1 was replaced with 30 g of the active ester (DIC company HP8000), and the rest remained unchanged.
- R is a phenyl group
- R1 is an azophosphine skeleton
- R2 is a phenyl group.
- the symbols in the table indicate no change, ⁇ indicates white spots, and X indicates stratification.
- the dielectric loss factor at 1 GHz was measured according to IPC-TM-650 2.5.5.5 according to the resonance method using a strip line.
- a 1.60 mm thick substrate was placed on a die of a certain pattern for punching, and the human eye was observed by the naked eye (hi), there was no white circle at the edge of the hole, (h2) a white circle was formed at the edge of the hole, and (h3) the edge of the hole was split, and the table was respectively separated.
- the active ester of phenoxycyclotriphosphazene is used, and the antimony and antimony atoms are more effective than the DIC 8000 active ester, and the flame retardant effect is better; and the active ester phase containing the phosphate ester of Comparative Example 4 Compared with the low water absorption rate, the present invention adopts phenoxycyclotriphosphazene active ester, which can achieve halogen-free flame retardant (halogen content within the requirements of JPCA halogen-free standard) without lowering the dielectric properties, and has excellent It has good heat resistance and good processability.
- halogen-free flame retardant halogen content within the requirements of JPCA halogen-free standard
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Laminated Bodies (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14894791.4A EP3037475A4 (en) | 2014-06-13 | 2014-06-13 | Phenoxy cyclotriphosphazene active ester, halogen-free resin composition and use thereof |
PCT/CN2014/079854 WO2015188377A1 (zh) | 2014-06-13 | 2014-06-13 | 一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 |
KR1020167021440A KR20160106673A (ko) | 2014-06-13 | 2014-06-13 | 페녹시 사이클로트리포스파젠 활성 에스테르, 무할로겐 수지 조성물 및 그 용도 |
US15/027,369 US20160244471A1 (en) | 2014-06-13 | 2014-06-13 | Phenoxycyclotriphosphazene active ester, halogen-free resin composition and uses thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2014/079854 WO2015188377A1 (zh) | 2014-06-13 | 2014-06-13 | 一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015188377A1 true WO2015188377A1 (zh) | 2015-12-17 |
Family
ID=54832750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2014/079854 WO2015188377A1 (zh) | 2014-06-13 | 2014-06-13 | 一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 |
Country Status (4)
Country | Link |
---|---|
US (1) | US20160244471A1 (zh) |
EP (1) | EP3037475A4 (zh) |
KR (1) | KR20160106673A (zh) |
WO (1) | WO2015188377A1 (zh) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106939016A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板、复合金属基板以及线路板 |
CN106939018A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板及复合金属基板 |
CN106939020A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板及复合金属基板 |
CN106939017A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板、复合金属基板以及线路板 |
CN106939022A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板及复合金属基板 |
EP3263576A1 (en) * | 2016-06-29 | 2018-01-03 | Guangdong Guangshan New Materials Co., Ltd. | Phosphazene compound containing ester group, preparation method and use thereof |
WO2018004273A1 (ko) * | 2016-06-27 | 2018-01-04 | 코오롱인더스트리 주식회사 | 열경화성 수지 조성물, 이를 이용한 프리프레그 및 기판 |
WO2018103199A1 (zh) * | 2016-12-07 | 2018-06-14 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN109439246A (zh) * | 2018-09-11 | 2019-03-08 | 法施达(大连)工程材料有限公司 | 一种双组份环氧结构胶黏剂及其制备方法 |
CN110785399A (zh) * | 2017-06-28 | 2020-02-11 | Dic株式会社 | 活性酯组合物和半导体密封材料 |
TWI728781B (zh) * | 2020-04-21 | 2021-05-21 | 穗曄實業股份有限公司 | 熱固型樹脂組成物 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108440735B (zh) * | 2018-04-24 | 2020-08-14 | 四川大学 | 含Diels-Alder键自修复阻燃聚氨酯弹性体及其制备方法 |
CN109294215B (zh) * | 2018-08-08 | 2020-11-20 | 万华化学集团股份有限公司 | 一种聚氨酯树脂组合料及用途和一种高强度高模量聚氨酯材料 |
CN109825081B (zh) * | 2019-01-30 | 2021-06-04 | 广东生益科技股份有限公司 | 一种热固性树脂组合物、包含其的预浸料以及覆金属箔层压板和印制电路板 |
CN112080111A (zh) * | 2020-08-18 | 2020-12-15 | 艾蒙特成都新材料科技有限公司 | 一种高耐热低介电环氧树脂组合物、层压板及其制备方法 |
CN114836147B (zh) * | 2022-04-21 | 2023-08-22 | 深圳市纽菲斯新材料科技有限公司 | 一种fc-bga封装载板用增层胶膜及使用其制作的涂胶铜箔 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012002119A1 (ja) * | 2010-07-02 | 2012-01-05 | Dic株式会社 | 熱硬化性樹脂組成物、その硬化物、活性エステル樹脂、半導体封止材料、プリプレグ、回路基板、及びビルドアップフィルム |
CN102977551A (zh) * | 2011-09-02 | 2013-03-20 | 广东生益科技股份有限公司 | 无卤树脂组合物以及使用其制作覆铜板的方法 |
CN103304962A (zh) * | 2013-06-20 | 2013-09-18 | 天津市凯华绝缘材料有限公司 | 一种具有优异的柔韧性和阻燃性的环氧树脂组合物及其制备方法 |
WO2013141247A1 (ja) * | 2012-03-21 | 2013-09-26 | Dic株式会社 | 活性エステル樹脂、熱硬化性樹脂組成物、その硬化物、半導体封止材料、プリプレグ、回路基板、及びビルドアップフィルム |
CN103665358A (zh) * | 2013-10-16 | 2014-03-26 | 上海大学 | 含有环三磷腈基团的磷氮共聚酯材料及其制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001151867A (ja) * | 1999-11-30 | 2001-06-05 | Hitachi Chem Co Ltd | 封止用エポキシ樹脂成形材料及び電子部品装置 |
TWI554541B (zh) * | 2011-05-10 | 2016-10-21 | Ajinomoto Kk | Resin composition |
JP5899497B2 (ja) * | 2011-08-31 | 2016-04-06 | パナソニックIpマネジメント株式会社 | 熱硬化性組成物、ワニス、プリプレグ、プリプレグの製造方法、金属張積層板、金属張積層板の製造方法、プリント配線板、及びプリント配線板の製造方法 |
US9005761B2 (en) * | 2011-12-22 | 2015-04-14 | Elite Material Co., Ltd. | Halogen-free resin composition and its application for copper clad laminate and printed circuit board |
CN103540101B (zh) * | 2012-07-17 | 2016-01-20 | 台光电子材料(昆山)有限公司 | 无卤素树脂组合物及应用其的铜箔基板及印刷电路板 |
-
2014
- 2014-06-13 KR KR1020167021440A patent/KR20160106673A/ko not_active Application Discontinuation
- 2014-06-13 WO PCT/CN2014/079854 patent/WO2015188377A1/zh active Application Filing
- 2014-06-13 US US15/027,369 patent/US20160244471A1/en not_active Abandoned
- 2014-06-13 EP EP14894791.4A patent/EP3037475A4/en not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012002119A1 (ja) * | 2010-07-02 | 2012-01-05 | Dic株式会社 | 熱硬化性樹脂組成物、その硬化物、活性エステル樹脂、半導体封止材料、プリプレグ、回路基板、及びビルドアップフィルム |
CN102977551A (zh) * | 2011-09-02 | 2013-03-20 | 广东生益科技股份有限公司 | 无卤树脂组合物以及使用其制作覆铜板的方法 |
WO2013141247A1 (ja) * | 2012-03-21 | 2013-09-26 | Dic株式会社 | 活性エステル樹脂、熱硬化性樹脂組成物、その硬化物、半導体封止材料、プリプレグ、回路基板、及びビルドアップフィルム |
CN103304962A (zh) * | 2013-06-20 | 2013-09-18 | 天津市凯华绝缘材料有限公司 | 一种具有优异的柔韧性和阻燃性的环氧树脂组合物及其制备方法 |
CN103665358A (zh) * | 2013-10-16 | 2014-03-26 | 上海大学 | 含有环三磷腈基团的磷氮共聚酯材料及其制备方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP3037475A4 * |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10233203B2 (en) | 2016-01-04 | 2019-03-19 | Guangdong Guangshan New Materials Co., Ltd. | Phosphazene compound, a prepreg and a composite metal laminate |
CN106939018A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板及复合金属基板 |
CN106939020A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板及复合金属基板 |
CN106939017A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板、复合金属基板以及线路板 |
CN106939022A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板及复合金属基板 |
CN106939016A (zh) * | 2016-01-04 | 2017-07-11 | 广东广山新材料股份有限公司 | 一种磷腈化合物、预浸板、复合金属基板以及线路板 |
US10774173B2 (en) | 2016-06-27 | 2020-09-15 | Kolon Industries, Inc. | Thermosetting resin composition, and prepreg and substrate using same |
KR20180001381A (ko) * | 2016-06-27 | 2018-01-04 | 코오롱인더스트리 주식회사 | 열경화성 수지 조성물, 이를 이용한 프리프레그 및 기판 |
CN109429496B (zh) * | 2016-06-27 | 2022-02-11 | 可隆工业株式会社 | 热固性树脂组合物以及使用其的预浸料和基板 |
KR102338982B1 (ko) * | 2016-06-27 | 2021-12-14 | 코오롱인더스트리 주식회사 | 열경화성 수지 조성물, 이를 이용한 프리프레그 및 기판 |
CN109429496A (zh) * | 2016-06-27 | 2019-03-05 | 可隆工业株式会社 | 热固性树脂组合物以及使用其的预浸料和基板 |
WO2018004273A1 (ko) * | 2016-06-27 | 2018-01-04 | 코오롱인더스트리 주식회사 | 열경화성 수지 조성물, 이를 이용한 프리프레그 및 기판 |
EP3263576A1 (en) * | 2016-06-29 | 2018-01-03 | Guangdong Guangshan New Materials Co., Ltd. | Phosphazene compound containing ester group, preparation method and use thereof |
CN108164685B (zh) * | 2016-12-07 | 2019-08-27 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108164685A (zh) * | 2016-12-07 | 2018-06-15 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
WO2018103199A1 (zh) * | 2016-12-07 | 2018-06-14 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN110785399A (zh) * | 2017-06-28 | 2020-02-11 | Dic株式会社 | 活性酯组合物和半导体密封材料 |
CN109439246A (zh) * | 2018-09-11 | 2019-03-08 | 法施达(大连)工程材料有限公司 | 一种双组份环氧结构胶黏剂及其制备方法 |
CN109439246B (zh) * | 2018-09-11 | 2021-04-23 | 法施达(大连)实业集团有限公司 | 一种双组份环氧结构胶黏剂及其制备方法 |
TWI728781B (zh) * | 2020-04-21 | 2021-05-21 | 穗曄實業股份有限公司 | 熱固型樹脂組成物 |
Also Published As
Publication number | Publication date |
---|---|
US20160244471A1 (en) | 2016-08-25 |
EP3037475A1 (en) | 2016-06-29 |
EP3037475A4 (en) | 2017-06-07 |
KR20160106673A (ko) | 2016-09-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2015188377A1 (zh) | 一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 | |
WO2013029271A1 (zh) | 无卤树脂组合物以及使用其制作覆铜板的方法 | |
KR101799717B1 (ko) | 열경화성 수지 조성물 및 그 용도 | |
TWI638001B (zh) | Thermosetting resin composition and use thereof | |
JP6085172B2 (ja) | 熱硬化性組成物 | |
WO2007094359A1 (ja) | セミipn型複合体の熱硬化性樹脂組成物並びにこれを用いたワニス、プリプレグ及び金属張積層板 | |
WO2012083728A1 (zh) | 无卤树脂组合物及使用其的无卤覆铜板的制作方法 | |
WO2012083727A1 (zh) | 无卤高tg树脂组合物及用其制成的预浸料与层压板 | |
KR101730283B1 (ko) | 열경화성 수지 조성물 및 그 용도 | |
WO2016049981A1 (zh) | 覆铜板用高cti无卤环氧树脂组合物及其应用 | |
WO2012083725A1 (zh) | 无卤阻燃性树脂组合物及其应用 | |
WO2011132408A1 (ja) | エポキシ樹脂組成物、プリプレグ、金属張積層板およびプリント配線板 | |
CN113121981B (zh) | 一种树脂组合物以及使用其的预浸片和绝缘板 | |
JP2006131743A (ja) | 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、プリント配線板 | |
CN110527037B (zh) | 一种无卤聚苯醚树脂组合物及使用其制作的半固化片和层压板 | |
WO2015154315A1 (zh) | 一种无卤无磷阻燃树脂组合物 | |
JP2016538363A (ja) | 相互進入高分子網目を形成する硬化性組成物 | |
CN109971175B (zh) | 改性马来酰亚胺树脂组合物及其制备的半固化片和层压板 | |
JP2003231762A (ja) | プリプレグ及び積層板 | |
CN110615876B (zh) | 无卤聚苯醚树脂组合物及使用其制作的半固化片和层压板 | |
JPH04258658A (ja) | 難燃性熱硬化性樹脂組成物 | |
WO2022244725A1 (ja) | 樹脂組成物、並びに、それを用いたプリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板及び配線基板 | |
WO2022210227A1 (ja) | 樹脂組成物、プリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板、及び配線板 | |
CN112824451B (zh) | 低介电树脂组合物、半固化片、及覆铜层压板 | |
JP4660953B2 (ja) | ジシアンジアミド付加リン変性エポキシ樹脂含有樹脂組成物およびその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14894791 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2014894791 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15027369 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 20167021440 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |