CN106928280A - 一种磷腈化合物、包含其的组合物、预浸板和线路板 - Google Patents
一种磷腈化合物、包含其的组合物、预浸板和线路板 Download PDFInfo
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- CN106928280A CN106928280A CN201511025327.5A CN201511025327A CN106928280A CN 106928280 A CN106928280 A CN 106928280A CN 201511025327 A CN201511025327 A CN 201511025327A CN 106928280 A CN106928280 A CN 106928280A
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- unsubstituted
- substituted
- alkyl
- combination
- aryl
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- -1 phosphazene compound Chemical class 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 26
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 10
- 239000002131 composite material Substances 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 239000003822 epoxy resin Substances 0.000 claims description 26
- 229920000647 polyepoxide Polymers 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 238000006467 substitution reaction Methods 0.000 claims description 22
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 20
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 230000000269 nucleophilic effect Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000004411 aluminium Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000011188 CEM-1 Substances 0.000 claims description 4
- 239000011190 CEM-3 Substances 0.000 claims description 4
- 101100257127 Caenorhabditis elegans sma-2 gene Proteins 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- UXJHQBVRZUANLK-UHFFFAOYSA-N azanylidyne(dichloro)-$l^{5}-phosphane Chemical compound ClP(Cl)#N UXJHQBVRZUANLK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 3
- 229910000838 Al alloy Inorganic materials 0.000 claims description 2
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 2
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 2
- 229910000640 Fe alloy Inorganic materials 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000004917 carbon fiber Substances 0.000 claims description 2
- 125000005587 carbonate group Chemical group 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000011152 fibreglass Substances 0.000 claims description 2
- 238000003754 machining Methods 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 238000003825 pressing Methods 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 abstract description 18
- 239000002585 base Substances 0.000 description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- SMYKVLBUSSNXMV-UHFFFAOYSA-K aluminum;trihydroxide;hydrate Chemical compound O.[OH-].[OH-].[OH-].[Al+3] SMYKVLBUSSNXMV-UHFFFAOYSA-K 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- GPRDLRZMTVQCHM-UHFFFAOYSA-L magnesium;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Mg+2] GPRDLRZMTVQCHM-UHFFFAOYSA-L 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- SPWIPDSCASBWFH-UHFFFAOYSA-N [P].N#CC#N Chemical compound [P].N#CC#N SPWIPDSCASBWFH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 230000037429 base substitution Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07F9/659—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 having three phosphorus atoms as ring hetero atoms in the same ring
-
- 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
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Abstract
本发明涉及一种磷腈化合物、及复合金属基板。该带羧酸酯的磷腈化合物具有式(Ⅰ)所示的分子结构。本发明通过采用特定组成的M基团得到带羧酸酯的磷腈化合物,其固化物具有良好的阻燃性、耐热性、机械性能、阻燃性以及低的介电常数,是一种具有较大的经济性及环保友好型的低介电的阻燃物质。
Description
技术领域
本发明属于阻燃物质的技术领域,尤其涉及带羧酸酯的磷腈化合物、包含其的组合物、预浸板和线路板。
背景技术
以手机、电脑、摄像机、电子游戏机为代表的电子产品、以空调、冰箱、电视影像、音响用品等为代表的家用、办公电器产品以及其他领域使用的各种产品,为了安全,很大部分的产品都要求其具备不同程度的阻燃性能。
为了使产品达到所要求的阻燃性能或等级,传统的技术常常使用向材料体系中添加如氢氧化铝水合物、氢氧化镁水合物等含有结晶水的金属氢氧化物等类的无机阻燃物质、和向体系材料中添加如溴化双酚A、溴化双酚A型环氧树脂等含溴量比较高的或含卤素量比较高的有机化学物质,为了提高这些含有卤素的有机化学物质的阻燃性,还常常在体系中再加入如三氧化二锑等对环境不友好的无机化学阻燃剂物质。
由于使用含卤素的阻燃物质,其燃烧时会产生无降解性或难降解的有毒物质如二恶英类有机卤素化学物质污染环境、影响人类及动物健康。
出于保护环境的目的,使用含磷、含氮等不含卤素的化合物代替含卤素化合物作为阻燃剂,特别是在电子、电气、电器产业上,采用具有反应性的单官能(一个分子中只有一个活性反应基团)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物以下简称DOPO),更多的是采用DOPO的衍生化合物作为阻燃成分,添加或不添加氢氧化铝水合物、氢氧化镁水合物达到阻燃的效果。
在电子领域,通常使用DOPO与线性酚醛型环氧树脂、邻甲基酚醛环氧树脂、双酚A酚醛型环氧树脂等高成本、多官能环氧树脂与DOPO反应的生成物(简称DOPO环氧树脂)广泛应用作为覆铜板用途的环氧树脂材料。
这些使用DOPO环氧树脂所制造的覆铜板,具有良好的阻燃性能,但黏结性、耐热性、加工性等存在不少的缺陷,不适合制造现代通信需要的高多层、高可靠性、高黏结性、良好的加工性能的需要,以及由于高成本的原因,不利于普及到如手机等要求低成本的消费电子等民用品领域。
在电子领域,通常使用DOPO与如双酚A、双酚F、酚醛树脂、苯酚、邻甲酚的醚化物反应制得含有DOPO骨架的含酚化合物(统称含磷酚醛树脂)当做环氧树脂固化剂或阻燃性物质添加剂,应用作为覆铜板用途的环氧树脂材料的阻燃剂。
这些使用含磷酚醛当做阻燃成分的一部分或全部所制得的覆铜板,可以达到阻燃的目的,但耐酸碱性、耐化学药品性、黏结性、耐热性、加工性等存在不少的缺陷,不适合制造现代通信需要的高多层、高可靠性、高黏结性、良好的加工性能的需要,以及由于高成本的原因,不利于普及到如手机等要求低成本的消费电子等民用品领域。
随着电子产业向短、小、薄、高多层化、高可靠性要求的进一步提高、民用消费电子的普及使用以及越来越严峻的环境污染的压力等因素的要求,市场迫切需要材料具有良好的阻燃性、耐热性、良好的机械性能的廉价阻燃性物质。
发明内容
有鉴于此,本发明一方面提供一种带羧酸酯的磷腈化合物,该磷腈化合物具有良好的阻燃性、耐热性、机械性能以及低的介电常数和介电损耗,而且,该磷腈化合物具有成本低的优势。
为了实现上述目的,本发明采用了如下技术方案:
一种带羧酸酯的磷腈化合物,其具有如式(Ⅰ)所示的分子结构:
式(Ⅰ)中,R1表示任意的有机基团,R为由亲核试剂提供的惰性亲核基团;M为环三磷腈基M1、环四以上磷腈基M2或非环状聚磷腈基M3中的任意一种或其至少两种的组合;
a为大于等于零的整数,例如0、1、2、3、4、5、6、7,c为大于等于1的整数,例如1、2、3、4、5、6、7,a和c之和大于或等于6;在本发明中,所述Ra中的“a”表示M基团中有a个R基团,该a个R基团的连接关系,本领域技术人员可根据卤代磷腈亲核取代原理得知。
在本发明中,R1表示任意的有机基团,条件是原子不超过正常价态,并且可以产生稳定的化合物。“稳定的化合物”是指能够足够强健地从反应混合物中分离至有效的纯度并配制成有效的化合物。
在本发明中,所述“惰性亲核基团”是指,一种官能团,其不带有活性基团,它不容易地或以一个实际的速度在常规的有机合成的条件下进行反应,其为亲核试剂与氯代磷腈化合物亲核取代反应后剩下的不含一般常识性反应的官能团。
优选地,式(Ⅰ)中,R1表示为脂肪烃基和/或芳烃基,优选为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或其至少两种的组合。
优选地,R1为未取代的直链烷基或支链烷基、未取代的环烷基、未取代的芳烷基、未取代的烷氧基、未取代的环烷氧基、未取代的芳烷氧基、未取代的烷基芳氧基、未取代的芳基或未取代的杂芳基中的任意一种或者至少两种的组合;
优选地,R1不含可以与环氧树脂反应生成二级羟基的反应性基团。
在本发明中,当a不为零时,表示该磷腈为R取代。在本发明中,所述亲核试剂即指,可以与卤代磷腈发生亲核取代反应的亲核试剂。在亲核取代反应过程中,亲核试剂脱去离去基团,亲核基团进攻卤代磷腈中的卤素原子,亲核基团和M相连。例如,当采用甲醇CH3OH作为亲核试剂与卤代磷腈发生亲核取代反应时,CH3OH脱去H+,甲氧基CH3O-取代卤代磷腈中的卤素原子,与磷腈中的-P相连,此时R即为CH3O-。
优选地,所述惰性亲核基团R具有结构Y-X-,所述X优选为O、C、N;所述Y为脂肪烃基和/或芳烃基,进一步优选取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或其至少两种的组合;
进一步优选地,R所述惰性亲核基团即R选自-OR13、-SR14、-C≡C-R18、R22-COO-、或中的任意一种或者至少两种的组合;
R13为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的碳酸酯基、取代或未取代的磺酸酯基、取代或未取代的膦酸酯基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R14为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R15、R16和R17均独立地为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种,R18为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R22为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R23和R24均独立地为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R26和R27均独立地为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合。
在前述记载中,取代或未取代的直链烷基或支链烷基优选为取代或未取代的C1~C12(例如C1、C2、C3、C4、C5、C6、C7、C8、C9、C10或C11)直链烷基或支链烷基,优选C1~C8直链烷基或支链烷基,当碳原子数为C1时即为甲基,碳原子数为C2时,即为乙基。
所述取代或未取代的环烷基优选为碳原子数为C3~C12(例如C4、C5、C6、C7、C8、C9、C10或C11)的取代或未取代的环烷基。
取代或未取代的芳基优选为苯基、苄基、1,2,3,4-四氢萘基,或等。苯基的实例包括联苯基、三联苯基、苯甲基、苯乙基或苯丙基等。
取代或未取代的杂芳基为五元或六元杂芳基。
取代或未取代的烷氧基为C1-C12(例如C1、C2、C3、C4、C5、C6、C7、C8、C9、C10或C11)烷氧基。
取代或未取代的芳烷基为C7-C12(例如C8、C9、C10或C11)芳烷基。
取代或未取代的环烷氧基为C3-C8(例如C4、C5、C6、C7或C8)环烷氧基。
取代或未取代的芳烷氧基为C7-C12(例如C8、C9、C10或C11)芳烷氧基。
取代或未取代的烷基芳氧基为C7-C12(例如C8、C9、C10或C11)烷基芳氧基。
优选地,所述R为取代或未取代的烷氧基或芳基氧基。
烷氧基的例子包括,但不限于甲氧基、乙氧基、异丙氧基、丙氧基、丁氧基和戊氧基。烷氧基团可以被下列取代基取代,如烯基、炔基、卤素、羟基、烷基羰氧基、芳基羰氧基、烷氧基羰氧基、芳氧基羰氧基、羧酸酯、烷基羰基、芳基羰基、烷氧基羰基、氨基羰基、烷基氨基羰基、二烷基氨基羰基、烷硫基羰基、烷氧基、磷酸酯、膦酸根合、次膦酸根合、氨基(包括烷基氨基、二烷基氨基、芳基氨基、二芳基氨基和烷基芳基氨基),酰氨基(包括烷基羰基氨基、芳基羰基氨基、氨基甲酰基和脲基)、脒基、亚氨基、巯基、硫代羧酸酯、硫酸酯、烷基亚磺酰基、磺酸基、氨磺酰基、磺酰氨基、硝基甲基、三氟甲基、氰基、叠氮基、杂环基、烷基芳基或芳族或杂芳族基团。卤素取代的烷氧基团的例子包括,但不限于一氟甲氧基、二氟甲氧基、三氟甲氧基、一氯甲氧基、二氯甲氧基、三氯甲氧基。
所述芳基氧基的实例包括苯氧基、苄氧基、萘氧基或联苯氧基,所述芳基氧基可以被烷基等取代。
在本发明中,优选地,M1结构为:
M2结构为:
其中,x大于等于4;
M3结构为:
其中,y大于等于3。
注意,M1、M2结构式的表示中,所出现符号仅仅是对“环状”结构的一种示意。M1、M2和M3中中P原子上连接的键仅代表三者中取代基取代发生在P原子上,不可理解为甲基的表示。
本发明另一方面提供一种带羧酸酯的磷腈化合物的制备方法,由该方法制备的磷腈化合物具有良好阻燃性、耐热性、良好的机械性能,且介电常数低。
一种制备上述述磷腈化合物的方法,将磷腈氯化物与亲核试剂进行亲核取代反应所得到。
亲核试剂为单官能酸。
该亲核取代反应中,氯被-COOR1所取代,产生氯化盐。亲核取代可采用本领域公知的方法来制备,例如可参考“聚磷腈的研究进展,张宏伟等,材料导报2010年第24卷第7期”。催化剂的具体实例有氯化锌、氯化镁、氯化铝等金属氯化物、三氟化硼及其络合物、氢氧化钠等路易斯碱。这些催化剂可以一种或多种混合使用,本发明中并无特别的规定。磷腈氯化物可以采用来源最为广泛的六氯环三磷腈等。为得到得到目标产物中的R基,可同时加入可提供R基的亲核试剂,例如R为烷氧基或者苯氧基,可通过加入甲醇或者苯酚进行混合取代,即氯原子同时被R和-COOR1同时取代。当然也可以先将六氯环三磷腈等用可提供-R基的亲核试剂取代部分氯原子后,再与亲核试剂反应。
在本发明中,所述磷腈化合物不含有卤素。
优选地,所述制备方法为将磷腈氯化物与R-Na反应后,再与R1COOH反应得到所述磷腈化合物。其中,所述R与R1具有与前述R与R1相同的意义。
本发明再一方面提供一种具有良好阻燃性、耐热性、良好的机械性能、低介电常数的环氧树脂组合物。
该环氧树脂组合物中加入上述带羧酸酯的磷腈化合物,作为阻燃剂。
至于环氧树脂组合物的环氧树脂、固化剂、其它填料可采用公知的环氧树脂。
所述环氧树脂组合物除前述含磷腈的聚酯外,还可以包括其他聚酯。
上述环氧树脂阻燃物可根据实际需要作为预浸板。
一种预浸板,其由如上述的带羧酸酯的磷腈化合物含浸或涂布于基材而成。
基材可以为玻璃纤维基材、聚酯基材、聚酰亚胺基材、陶瓷基材或碳纤维基材等。
这里,其含浸或涂布的具体工艺条件无特别限定。“预浸板”也为本领域技术人员所熟知的“粘结片”。
一种复合金属基板,其包括一张以上如上述预浸板依次进行表面覆金属层重叠、压合而成。
这里,表面覆金属层的材质为铝、铜、铁及其任意组合的合金。
复合金属基板的具体实例有CEM-1覆铜板、CEM-3覆铜板、FR-4覆铜板、FR-5覆铜板、CEM-1铝基板、CEM-3铝基板、FR-4铝基板或FR-5铝基板。
一种线路板,于上述的复合金属基板的表面加工线路而成。
环氧树脂组合物的原料通过固化在复合金属基板上形成具有良好阻燃性能的涂层,可提高线路板,例如电子产业、电气、电器产业、交通运输、航空航天、玩具产业等需要线路板的机器、设备、仪器、仪表等产业的广泛应用。
上述术语“×××基或基团”指×××化合物分子结构中脱去一个或多个氢原子或其它原子或原子团后剩余的部分。
本发明通过采用特定组成的M基团得到阻燃化合物,使得该阻燃性化合物具有良好的阻燃性,其固化物具有良好的阻燃性、耐热性、机械性能以及、低的介电常数和介电损耗,是一种还具有较大的经济性及环保友好型的低介电的阻燃物质。
具体实施方式
下面结合实施例来进一步说明本发明的技术方案。
实施例1
本实施例磷腈化合物的结构式如下:
带有搅拌装置的三口2000ml玻璃反应器里投入六氯环三磷腈1mol、丙酮200ml、苯甲酸6mol,一边搅拌、一边通氮气、一升温到60℃,用60min滴入20%氢氧化钠溶液620g,保持60℃温度,搅拌反应15个小时。反应后,用物理方法去除体系中的盐分、水分,再过滤去除体系中的不溶物质,蒸馏掉体系中溶剂,得到低介电的阻燃化合物,测得其酯当量为150g/eq,将此目的生成物命名为A。
以上述A生成物150g(1eq)、环氧当量为200g/eq的邻甲酚醛环氧树脂200g(1eq),和0.2g的吡啶,用适量的丁酮溶解成溶液,用标准玻璃布,按照常规的制作方法,得到含树脂量为50%的覆铜板a,覆铜板a的各项性能在表-1中表示。
对得到的化合物A进行核磁共振氢谱表征,结果如下:
1H NMR(CDCl3,500MHz):8.13,(s,12H,酯基邻位苯基上的氢),7.47(m,12H,酯基间位苯基上的氢),7.60(m,6H,酯基对位苯基上的氢)。
红外谱图特征峰的位置:酯羰基1730-1740cm-1,酯基的C-O-C 1200cm-1。
实施例2
本实施例磷腈化合物的结构式如下:
带有搅拌装置的三口2000ml玻璃反应器里投入六氯环三磷腈1mol、丙酮200ml、苯甲酸3mol,甲醇钠3mol,一边搅拌、一边通氮气、一升温到60℃,用60min滴入20%氢氧化钠溶液620g,保持60℃温度,搅拌反应15个小时。反应后,用物理方法去除体系中的盐分、水分,再过滤去除体系中的不溶物质,蒸馏掉体系中溶剂,得到阻燃化合物1mol,测得其酯当量为80g/eq。将此目的生成物命名为B。
对得到的化合物B进行核磁共振氢谱表征,结果如下:
1H NMR(CDCl3,500MHz):3.39(m,15H,甲基的氢),8.13,(s,2h,酯基邻位苯基上的氢),7.47(m,2H,酯基间位苯基上的氢),7.60(m,1H,酯基对位苯基上的氢)。
红外谱图特征峰的位置:酯羰基1730-1740cm-1,酯基的C-O-C 1200cm-1。
以上述B生成物1125g中入环氧当量为200g/eq的邻甲酚醛环氧树脂100g,和0.2g的吡啶,用适量的丁酮溶解成溶液,用标准玻璃布,按照常规的制作方法,得到含树脂量为50%的覆铜板b,覆铜板b的各项性能在表-1中表示。
实施例3
以上述A生成物75g和如下式所示的酯当量为220g/eq酯化合物(广东广山新材料有限公司产品YEH-6611)110g中入、环氧当量为200g/eq的双酚A酚醛环氧树脂200,和0.2g的吡啶,用适量的丁酮溶解成溶液,用标准玻璃布,按照常规的制作方法,得到含树脂量为50%的覆铜板c,覆铜板c的各项性能在表-1中表示。
比较例1
在环氧当量为200g/eq的邻甲基酚醛环氧树脂200g,加入酚羟基当量为105g/eq的线型酚醛树脂固化剂105g和作为阻燃剂的六苯氧基磷氰70g以及0.2g的2-甲基咪唑,用适量的丁酮溶解成溶液,用标准玻璃布,按照常规的制作方法,得到含树脂量为50%的覆铜板d,覆铜板d的各项性能在表-1中表示。
比较例2
在环氧当量为200g/eq的邻甲基酚醛环氧树脂200g、作为阻燃剂的六苯氧基磷氰70g、YEH-6611220g以及0.2g的吡啶,用适量的丁酮溶解成溶液,用标准玻璃布,按照常规的制作方法,得到含树脂量为50%的覆铜板e,覆铜板e的各项性能在表-1中表示。
实施例和比较例的测试结果如下表-1所示(鉴于具体测试方法已为本领域技术人员所熟知,在此对方法不再详述):
表-1,各种覆铜板的性能比较
申请人声明,本发明通过上述实施例来说明本发明的详细工艺设备和工艺流程,但本发明并不局限于上述详细工艺设备和工艺流程,即不意味着本发明必须依赖上述详细工艺设备和工艺流程才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (9)
1.一种磷腈化合物,其特征在于,其具有如式(Ⅰ)所示的分子结构:
式(Ⅰ)中,R1表示任意的有机基团,R为由亲核试剂提供的惰性亲核基团;M为环三磷腈基M1、环四以上磷腈基M2或非环状聚磷腈基M3中的任意一种或其至少两种的组合;
a为大于等于零的整数,c为大于等于1的整数,a和c之和大于或等于6。
2.如权利要求1所述的磷腈化合物,其特征在于,R1为脂肪烃基和/或芳烃基,进一步优选取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或其至少两种的组合;
优选地,R1为未取代的直链烷基或支链烷基、未取代的环烷基、未取代的芳烷基、未取代的烷氧基、未取代的环烷氧基、未取代的芳烷氧基、未取代的烷基芳氧基、未取代的芳基或未取代的杂芳基中的任意一种或者至少两种的组合;
优选地,R1不含可以与环氧树脂反应生成二级羟基的反应性基团;
优选地,所述惰性亲核基团R具有结构Y-X-,所述X优选为O、C、N;所述Y为脂肪烃基和/或芳烃基,进一步优选取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或其至少两种的组合;
进一步优选地,R选自-OR13、-C≡C-R18、R22-COO-、中的任意一种或者至少两种的组合;
R13为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的碳酸酯基、取代或未取代的磺酸酯基、取代或未取代的膦酸酯基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R14为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R15、R16和R17均独立地为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R18为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R22为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R23和R24均独立地为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合,R26和R27均独立地为取代或未取代的直链烷基或支链烷基、取代或未取代的环烷基、取代或未取代的芳烷基、取代或未取代的烷氧基、取代或未取代的环烷氧基、取代或未取代的芳烷氧基、取代或未取代的烷基芳氧基、取代或未取代的芳基或取代或未取代的杂芳基中的任意一种或者至少两种的组合;
优选地,所述磷腈化合物为具有如下结构的磷腈化合物中的任意一种或者至少两种的混合物:
3.根据权利要求1或2所述的带羧酸酯的磷腈化合物,其特征在于,M1结构为:
M2结构为:
其中,x大于等于4;
M3结构为:
其中,y大于等于3。
4.一种如权利要求1-3之一所述磷腈化合物的制备方法,其特征在于,将磷腈氯化物与亲核试剂进行亲核取代反应所得到;
优选地,所述制备方法为将磷腈氯化物与R-Na反应后,再与R1COOH反应得到权利要求1-3之一所述磷腈化合物。
5.一种环氧树脂组合物,其特征在于,包含权利要求1-3之一所述的带羧酸酯的磷腈化合物。
6.一种预浸板,其特征在于,其由如权利要求5所述环氧树脂组合物含浸或涂布于基材而成。
7.如权利要求6所述的预浸板,其特征在于,所述基材为玻璃纤维基材、聚酯基材、聚酰亚胺基材、陶瓷基材或碳纤维基材。
8.一种复合金属基板,其特征在于,其包括一张以上如权利要求5或6所述预浸板依次进行表面覆金属层、重叠、压合而成;
优选地,所述表面覆金属层的材质为铝、铜、铁及其任意组合的合金;
优选地,所述复合金属基板为CEM-1覆铜板、CEM-3覆铜板、FR-4覆铜板、FR-5覆铜板、CEM-1铝基板、CEM-3铝基板、FR-4铝基板或FR-5铝基板。
9.一种线路板,其特征在于,于权利要求8所述的复合金属基板的表面加工线路而成。
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