CN105646588A - Phosphazene compound with carboxylic ester, presoaked plate, composite metal substrate and circuit board - Google Patents
Phosphazene compound with carboxylic ester, presoaked plate, composite metal substrate and circuit board Download PDFInfo
- Publication number
- CN105646588A CN105646588A CN201610029549.2A CN201610029549A CN105646588A CN 105646588 A CN105646588 A CN 105646588A CN 201610029549 A CN201610029549 A CN 201610029549A CN 105646588 A CN105646588 A CN 105646588A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- straight chained
- aralkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 Phosphazene compound Chemical class 0.000 title claims abstract description 47
- 239000000758 substrate Substances 0.000 title claims abstract description 16
- 239000002131 composite material Substances 0.000 title claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 13
- 239000002184 metal Substances 0.000 title claims abstract description 13
- 150000001733 carboxylic acid esters Chemical class 0.000 title abstract 5
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 150000007942 carboxylates Chemical class 0.000 claims description 23
- 239000003822 epoxy resin Substances 0.000 claims description 23
- 229920000647 polyepoxide Polymers 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 10
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 8
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 8
- 239000004411 aluminium Substances 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004437 phosphorous atom Chemical group 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 5
- 239000011188 CEM-1 Substances 0.000 claims description 4
- 239000011190 CEM-3 Substances 0.000 claims description 4
- 101100257127 Caenorhabditis elegans sma-2 gene Proteins 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- UXJHQBVRZUANLK-UHFFFAOYSA-N azanylidyne(dichloro)-$l^{5}-phosphane Chemical compound ClP(Cl)#N UXJHQBVRZUANLK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 239000000956 alloy Substances 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims description 2
- 239000004917 carbon fiber Substances 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000011889 copper foil 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
- 229920001721 polyimide Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000003825 pressing Methods 0.000 claims description 2
- 239000003989 dielectric material Substances 0.000 abstract description 3
- 239000002585 base Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical group CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000004185 ester group Chemical group 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000000269 nucleophilic effect Effects 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000053 physical method Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229940005657 pyrophosphoric acid Drugs 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 0 C*c1ccc(*CCc(cc2)ccc2I*)cc1 Chemical compound C*c1ccc(*CCc(cc2)ccc2I*)cc1 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- SPWIPDSCASBWFH-UHFFFAOYSA-N [P].N#CC#N Chemical compound [P].N#CC#N SPWIPDSCASBWFH-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-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
- 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
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 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
- 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
- HXOPNGMQXNNEGW-UHFFFAOYSA-N CC(C)(N)N=P(C)(C)C(C)(C)N Chemical compound CC(C)(N)N=P(C)(C)C(C)(C)N HXOPNGMQXNNEGW-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 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
- 239000002879 Lewis base Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical group [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 description 1
- INKDAKMSOSCDGL-UHFFFAOYSA-N [O].OC1=CC=CC=C1 Chemical compound [O].OC1=CC=CC=C1 INKDAKMSOSCDGL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004457 alkyl amino carbonyl 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
- 125000003806 alkyl carbonyl amino 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
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 230000005540 biological transmission 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
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 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
- 230000007613 environmental effect Effects 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
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 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
- 229910052727 yttrium Inorganic materials 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
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/09—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B9/00—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00
- B32B9/005—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00 comprising one layer of ceramic material, e.g. porcelain, ceramic tile
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B9/00—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00
- B32B9/005—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00 comprising one layer of ceramic material, e.g. porcelain, ceramic tile
- B32B9/007—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00 comprising one layer of ceramic material, e.g. porcelain, ceramic tile comprising carbon, e.g. graphite, composite carbon
-
- 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
- C08G59/40—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 curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4238—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D185/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Coating compositions based on derivatives of such polymers
- C09D185/02—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Coating compositions based on derivatives of such polymers containing phosphorus
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
- B32B2255/02—Coating on the layer surface on fibrous or filamentary layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
- B32B2255/10—Coating on the layer surface on synthetic resin layer or on natural or synthetic rubber layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
- B32B2255/26—Polymeric coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/02—Composition of the impregnated, bonded or embedded layer
- B32B2260/021—Fibrous or filamentary layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/106—Carbon fibres, e.g. graphite fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/07—Parts immersed or impregnated in a matrix
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2311/00—Metals, their alloys or their compounds
- B32B2311/12—Copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2313/00—Elements other than metals
- B32B2313/04—Carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2315/00—Other materials containing non-metallic inorganic compounds not provided for in groups B32B2311/00 - B32B2313/04
- B32B2315/02—Ceramics
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2333/00—Polymers of unsaturated acids or derivatives thereof
- B32B2333/04—Polymers of esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Ceramic Engineering (AREA)
- Medicinal Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
Abstract
The invention relates to a phosphazene compound with carboxylic ester, a presoaked plate, a composite metal substrate and a circuit board. The phosphazene compound with carboxylic ester has the molecular structure shown in formula (I). The phosphazene compound with carboxylic ester is obtained through special-composition M groups, and cured matter of the phosphazene compound with carboxylic ester has low dielectric properties and good heat resistance and mechanical properties and is a low dielectric material which is high in economical efficiency and environmentally friendly.
Description
Technical field
The invention belongs to dielectric materials technical field, relate to a kind of with the phosphazene compound of carboxylate, pre-impregnated sheet, composite metal substrate and wiring board.
Background technology
With mobile phone, computer, video camera, electronic game machine be representative electronic product, with air-conditioning, refrigerator, television image, sound equipment articles for use etc. be representative domestic, office electric equipment products and other field use various products, for safety, significant portion of product is desirable that it possesses low-dielectric and thermostability.
For electrical properties, the factor that mainly need to consider also includes dielectric constant and the dielectric loss of material. Generally, due to the square root of the dielectric constant of the signal transfer rate of substrate and baseplate material is inversely proportional to, therefore the dielectric constant of baseplate material is generally the smaller the better; On the other hand, the loss representing signal transmission owing to dielectric loss is more little is more few, therefore the transmission quality that the less material of dielectric loss can be provided by is also comparatively good.
Therefore, how to develop the material with low-k and low-dielectric loss, and be applied to the manufacture of high frequency printed circuit board, be present stage printed circuit board material field problem demanding prompt solution.
Summary of the invention
In view of this, one aspect of the present invention provides a kind of phosphazene compound with carboxylate, and this phosphazene compound has good heat resistance, mechanical performance and low dielectric constant and dielectric loss, and, this phosphazene compound has the advantage that cost is low.
To achieve these goals, present invention employs following technical scheme:
A kind of phosphazene compound with carboxylate, it has the molecular structure as shown in formula I:
In formula I, R1Representing arbitrary organic group, Y is arbitrary organic group, and R is inertia end-capping group; M is ring three phosphonitrile base M1, ring more than four phosphonitrile base M2Or non-annularity polyphosphazene base M3In the combination of any one or its at least two;
A is the integer be more than or equal to zero, for instance 0,1,2,3,4,5,6,7, c is the integer be more than or equal to 1, for instance 1,2,3,4,5,6,7, and a and c sum is equal in M group 2 times of number of phosphorus atoms; In the present invention, described RaIn " a " represent that M group has a R group, the annexation of this R group, those skilled in the art can learn according to halo phosphonitrile nucleophilic displacement of fluorine principle.
In the present invention, described (-Y-COOR1) " c " in c represent there be c-Y-COOR in M group1Group.
R and Y-COOR1It is connected on the phosphorus atoms of M, R and Y--COOR1In any two can be simultaneously connected with on the same phosphorus atoms of M, it is also possible to be connected on the different phosphate atom of M.
In the present invention, R1Represent arbitrary organic group, condition be atom less than normal valency, and stable compound can be produced. " stable compound " refers to enough separate from reactant mixture to effective purity con vigore and be configured to compounds effective.
Exemplary Y-COOR1It is such as-NH-A-COOR1, wherein, A is phenyl.
In the present invention, described " inertia end-capping group " refers to, a kind of functional group, it is without active group, it does not allow to change places or react when conventional organic synthesis with an actual speed, and it is the remaining functional group reacted without general common-sense after nucleopilic reagent and chloro phosphazene compound nucleophilic substitution.
Preferably, in formula I, R1Represent the combination of any one or its at least two in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
Preferably, in formula I, Y is selected from any one in group:
-O-R2-��-OOC-R3-or
Wherein, R2��R3And R4Combination independently selected from any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or at least two.
In the present invention, when a is not zero, represent that this phosphonitrile is that R replaces. In the present invention, namely described nucleopilic reagent refers to, it is possible to the nucleopilic reagent of halo phosphonitrile generation nucleophilic substitution. In nucleophilic substitution process, leaving group sloughed by nucleopilic reagent, and the halogen atom in nucleophilic group attack halo phosphonitrile, nucleophilic group is connected with M. Such as, when adopting methanol CH3When OH is as nucleopilic reagent and halo phosphonitrile generation nucleophilic substitution, CH3OH sloughs H+, methoxyl group CH3O-replaces the halogen atom in halo phosphonitrile, is connected with-the P in phosphonitrile, and now R is CH3O-��
In the present invention, when adopting same nucleopilic reagent to carry out nucleophilic substitution, now R and-Y-COOR1Identical. When adopting different nucleopilic reagents to carry out nucleophilic substitution reaction, R and-Y-COOR1Differ. Such as, can first adopting methanol nucleophilic displacement of fluorine part chlorine, now R is CH3O-. Then the nucleopilic reagent nucleophilic displacement of fluorine chlorine containing carboxylic acid ester groups is adopted again.
In the present invention, described R is inertia end-capping group. Described " inertia end-capping group " refers to, a kind of functional group, it is without active group, it does not allow to change places or react when conventional organic synthesis with an actual speed, and it is the remaining functional group reacted without general common-sense after nucleopilic reagent and chloro phosphazene compound nucleophilic substitution.
Nucleopilic reagent containing hydroxyl such as alcohols or aldehydes matter, for instance methanol, ethanol, propanol, phenol or hydroquinone etc., now R is CH3O-��CH3CH2-O-��CH3CH2CH-O-, phenoxy group or para hydroxybenzene oxygen base.
In the present invention, it is preferred to, described inertia end-capping group and R are selected from-OR13��-C��C-R18��R22-COO-��In any one or the combination of at least two in the combination of any one or at least two;
R13For the combination of any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryloxy alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl or at least two, R15��R16And R17All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, R18For the combination of any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl or at least two, R22For any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R23And R24All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, R26And R27All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, R27For any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
In foregoing description, substituted or unsubstituted straight chained alkyl or branched alkyl are preferably substituted or unsubstituted C1��C12 (such as C1, C2, C3, C4, C5, C6, C7, C8, C9, C10 or C11) straight chained alkyl or branched alkyl, preferred C1��C8 straight chained alkyl or branched alkyl, it is methyl when carbon number is C1, when carbon number is C2, it is ethyl.
Described substituted or unsubstituted cycloalkyl is preferably the substituted or unsubstituted cycloalkyl that carbon number is C3��C12 (such as C4, C5, C6, C7, C8, C9, C10 or C11).
Substituted or unsubstituted aryl is preferably phenyl, benzyl, 1,2,3,4-tetralyl,Deng. The example of phenyl includes xenyl, terphenyl, benzyl, phenethyl or phenylpropyl etc.
Substituted or unsubstituted heteroaryl is five yuan or six membered heteroaryl.
Substituted or unsubstituted aralkyl is C7-C12 (such as C8, C9, C10 or C11) aralkyl.
Substituted or unsubstituted aryloxy alkyl is C7-C13 (such as C8, C9, C10, C11 or C12) aryloxy alkyl.
Preferably, described R is substituted or unsubstituted alkoxyl or aryloxy group.
The example of alkoxyl includes, but are not limited to methoxyl group, ethyoxyl, isopropoxy, propoxyl group, butoxy and amoxy. alkoxy grp can be replaced by substituents, such as thiazolinyl, alkynyl, halogen, hydroxyl, alkyl carbonyl oxy, aryl-carbonyl oxygen, alkoxyl carbonyl oxygen base, aryloxy group carbonyl oxygen base, carboxylate, alkyl-carbonyl, aryl carbonyl, alkoxy carbonyl, amino carbonyl, alkyl amino-carbonyl, dialkyl amino carbonyl, alkylthiocarbonyl, alkoxyl, phosphate ester, phosphonate radical closes, phosphinic acid root closes, amino (includes alkyl amino, dialkyl amido, arylamino, ammonia diaryl base and alkyl aryl amino), acylamino-(includes alkyl-carbonyl-amino, aryl-amino-carbonyl, carbamoyl and urea groups), amidino groups, imino group, sulfydryl, alkylthio group, arylthio, carbothioic acid ester, sulfuric ester, alkyl sulphinyl, sulfonic group, sulfamoyl, sulfonamido, nitromethyla, trifluoromethyl, cyano group, azido, heterocyclic radical, alkylaryl or aromatics or heteroaromatic group. the example of the alkoxy grp of halogen substiuted includes, but are not limited to a fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, a chlorine methoxyl group, dichloro methoxyl group, trichloromethoxy.
The example of described aryloxy group includes phenoxy group, benzyloxy, naphthoxy or biphenylyloxy, and described aryloxy can be replaced by alkyl etc.
Preferably, the combination of any one or at least two that Y is selected from group:
R4The combination of any one or at least two in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;
R5��R6And R9All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one;
R7And R8All independently be in H, substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, and R7And R8It is asynchronously H;Work as R7And R8In all without H time, then represent two hydroxyl hydrogens in phosphoric acid respectively by R7And R8Replace; Work as R7And R8During middle only one of which H, then represent the only one of which hydroxyl hydrogen in phosphoric acid by R7Or R8Replace;
R10��R11And R12All independently be in H, substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, and R10��R11And R12In at most have two for H; Work as R10��R11And R12In when all there is no H, represent three hydroxyl hydrogens of pyrophosphoric acid respectively by R10��R11And R12Replace; Work as R10��R11��R12During middle only one of which H, represent two hydroxyl hydrogens of pyrophosphoric acid by R10��R11Or R12In two replacements; Work as R10��R11And R12In when having two H, represent a hydroxyl hydrogen of pyrophosphoric acid by R10��R11Or R12In any one replace.
Term used in the present invention " replacement " refers to that any one or more hydrogen atoms on specified atom are selected from the substituent group of designated groups and replace, and condition is described specified atom less than normal valency, and the result replaced is to produce stable compound. When substituent group is oxo group or ketone group (namely=O), then 2 hydrogen atoms on atom are replaced. Ketone substituent group is absent from aromatic rings. " stable compound " refers to enough separate from reactant mixture to effective purity con vigore and be configured to compounds effective.
In the present invention, it is preferred to, M1Structure is:
M2Structure is:
Wherein, x is be more than or equal to 4;
M3Structure is:
Wherein, y is be more than or equal to 3.
Note, M1��M2In the expression of structural formula, occurred symbolIt it is only a kind of signal to " ring-type " structure. M1��M2And M3InThe key connected on middle P atom only represents substituent group in three and replaces generation on P atom, the unintelligible expression for methyl.
Preferably, M represents the group of the phosphorus nitrogen skeleton being mainly made up of unsaturated phosphorus and nitrogen-atoms, i.e. phosphazenium groups, particularly as follows: M comprises the ring three phosphonitrile base M of at least 50wt%1, at most 48wt% ring more than four phosphonitrile base M2And the non-annularity polyphosphazene base M of at most 48wt%3��
In the present invention, M1Content is at least 50wt%, i.e. M1Content can be 50wt��100wt%, M1For bulk composition. Work as M1When content is 100wt%, then do not contain M2And M3. The typical but non-limiting M of the present invention1Content can be 50wt%, 51wt%, 55wt%, 58wt%, 60wt%, 65wt%, 70wt%, 74wt%, 75wt%, 80wt%, 85wt%, 90wt%, 92wt%, 95wt%, 98wt% or 100wt%.
In the present invention, M2Content is at most 48wt%, namely refers to, M2Content can be 0��48wt%. Work as M2When content is 0wt%, namely refer to, do not contain M2. The typical but non-limiting M of the present invention2Content can be 0wt%, 2wt%, 5wt%, 8wt%, 11wt%, 14wt%, 17wt%, 20wt%, 23wt%, 26wt%, 29wt%, 32wt%, 35wt%, 38wt%, 42wt%, 45wt% or 48wt%.
In the present invention, M3Content is at most 48wt%, namely refers to, M3Content can be 0��48wt%. Work as M3When content is 0wt%, namely refer to, do not contain M3. The typical but non-limiting M of the present invention3Content can be 0wt%, 2wt%, 5wt%, 8wt%, 11wt%, 14wt%, 17wt%, 20wt%, 23wt%, 26wt%, 29wt%, 32wt%, 35wt%, 38wt%, 42wt%, 45wt% or 48wt%.
In the present invention, if M1Content is less than 50wt%, or M2More than 48wt%, then in use all can damage thermostability, resistance to water and mechanical performance with the reacted product of epoxy resin. If M3Content more than 48%, then with the reacted product of epoxy resin in use it would be possible to cause because viscosity is excessive using inconvenience, and makes the bad results such as its performance suffers damage because molecular weight is excessive.
The preparation method that another aspect of the present invention provides a kind of phosphazene compound with carboxylate, the method the phosphazene compound prepared has good heat resistance and mechanical performance, and dielectric constant is low.
A kind of prepare the above-mentioned method stating phosphazene compound, by phosphonitrile chloride with to carry out nucleophilic substitution containing carboxylate compound nucleopilic reagent obtained.
Phosphonitrile chloride refers to Ra-M-Cle, it is the compound being structured with formula: H-Y-COOR containing carboxylate compound1; Note, to above-mentioned R1, M, a, Y restriction with aforementioned formula I, e is the integer equal to c.
In this nucleophilic substitution, chlorine is by-Y-COOR1Replaced, produce chlorate. Nucleophilic displacement of fluorine can adopt method well known in the art to prepare, for instance is referred to " progress of polyphosphazene, Zhang Hongwei etc., material Leader the 24th volume the 7th phase in 2010 ". The instantiation of catalyst has metal chloride, boron trifluoride and the lewis bases such as complex, sodium hydroxide thereof such as zinc chloride, magnesium chloride, aluminum chloride. These catalyst can use in one or more mixing, there is no special regulation in the present invention. Phosphonitrile chloride can adopt the most commonly used hexachlorocyclotriph,sphazene in source etc. For obtaining the R base in target product, can being simultaneously introduced the nucleopilic reagent that can provide R base, for instance R is alkoxyl or phenoxy group, can carry out mixing by addition methanol or phenol and replace, namely chlorine atom is simultaneously by R and-Y-COOR1Replace simultaneously. After first hexachlorocyclotriph,sphazene etc. can certainly being replaced part chlorine atom with the nucleopilic reagent that can provide-R base, then react with containing carboxylate compound.
Further aspect of the present invention provides a kind of composition epoxy resin with good thermostability, good mechanical performance, low-k.
This composition epoxy resin adds the above-mentioned phosphazene compound with carboxylate, as firming agent.
Known epoxy resin can be adopted as the epoxy resin of composition epoxy resin, firming agent, other filler.
Described composition epoxy resin is except the aforementioned polyester containing phosphonitrile, it is also possible to include other polyester.
Above-mentioned composition epoxy resin can according to actual needs as pre-impregnated sheet.
A kind of pre-impregnated sheet, it is impregnated with by the phosphazene compound with carboxylate described above or is coated base material and forms.
Base material can be fiberglass substrate, polyester base material, polyimide base material, ceramic base material or carbon fiber base material etc.
Here, the concrete technology condition of its impregnation or coating is not particularly limited. " bonding sheet " that " pre-impregnated sheet " is also well known to those skilled in the art.
A kind of composite metal substrate, it includes more than one as above-mentioned pre-impregnated sheet is sequentially carried out surface metal-clad overlap, pressing forms.
Here, the material of surface metal-clad is the alloy of aluminum, copper, ferrum and combination in any thereof.
The instantiation of composite metal substrate has CEM-1 copper-clad plate, CEM-3 copper-clad plate, FR-4 copper-clad plate, FR-5 copper-clad plate, CEM-1 aluminium base, CEM-3 aluminium base, FR-4 aluminium base or FR-5 aluminium base.
The invention provides a kind of flexible copper-clad plate, described flexible copper-clad plate comprise more than one pre-impregnated sheet of the present invention and be overlying on overlapping after the Copper Foil of pre-impregnated sheet one or both sides.
A kind of wiring board, the Surface Machining circuit in above-mentioned composite metal substrate forms.
The raw material of composition epoxy resin forms the coating with low-dielectric energy by being solidificated on composite metal substrate, wiring board can be improved, for instance electronic industry, electrically, Electric Industrial, transportation, Aero-Space, toy industry etc. need the extensive use of the industries such as the machine of wiring board, equipment, instrument, instrument.
Above-mentioned term " ������ base or group " refers to slough in ������ molecular structure of compounds remaining part after one or more hydrogen atom or other atom or atomic group.
In the present invention, namely described Ph represents phenyl.
The present invention obtains the phosphazene compound with carboxylate by adopting the M group of specific composition, this compound is made to have good low-dielectric energy, its solidfied material has good thermostability, mechanical performance and low dielectric constant and dielectric loss, is a kind of dielectric materials also with bigger economy and environmental protection friendly. The dielectric constant (1GHz) adopting the copper-clad plate that this resin combination obtains is 3.0-3.1, dielectric loss (1GHz) for 0.004-0.006, Tg can reach 170 DEG C and more than, T-peel strength can reach 1.90kg/mm2And more than, interlaminar strength can reach 1.63kg/mm2And more than, saturated water absorption can reach less than 0.35%.
Detailed description of the invention
Technical scheme is further illustrated below in conjunction with embodiment.
Embodiment 1
The structural formula of the present embodiment phosphazene compound with carboxylate is as follows:
Put into hexachlorocyclotriph,sphazene 1mol, acetone 200ml, methyl parahydroxybenzoate 3mol and Feldalat NM 3mol in three mouthfuls of 2000ml glass reactors with agitating device and stir while leading to nitrogen, it is warmed up to 60 DEG C, 20% sodium hydroxide solution 620g is instilled with 60min, keep 60 DEG C of temperature, stirring reaction 15 hours. After reaction, with the impurity in physical method removal system and moisture, distill solvent in system, obtain the carboxylate A1mol that ester equivalent is 236g/eq of said structure.
The compound A obtained is carried out proton nmr spectra sign, and result is as follows:
1HNMR(CDCl3, 500MHz): 7.80, (s, 6H, the hydrogen on the phenyl of ester group ortho position), and 6.84 (m, 6H, the hydrogen on the phenyl of position between ester group), 3.88 (m, 9H, the hydrogen of the methyl being connected with ester group), 3.39 (m, 9H, OCH3)��
The position of infrared spectrum characteristic peak: ester carbonyl group 1730-1740cm-1, the C-O-C1200cm of ester group-1, the characteristic absorption peak 1217cm of P=N key in phosphazene backbone-1, P-N874cm in phosphazene backbone-1, the characteristic absorption peak 1217cm of P=N key in phosphazene backbone-1, P-N874cm in phosphazene backbone-1, the absworption peak 2995.3cm of methyl ether-1, P-O-C key absworption peak 1035cm-1��
Add, as firming agent, o-cresol formaldehyde epoxy resin 100g, the curing accelerator pyridine 0.2g that epoxide equivalent is 200g/eq using above-mentioned carboxylate A118g, prepare composition epoxy resin. Adopting this composition epoxy resin to prepare the standard copper-clad plate sample meeting the standard such as GB, UL, called after a copper-clad plate according to general copper-clad plate production process, the performance of test a copper-clad plate, its result represents in table-1.
Embodiment 2
The structural formula of the present embodiment phosphazene compound with carboxylate is as follows:
In three mouthfuls of 2000ml glass reactors with agitating device put into hexachlorocyclotriph,sphazene 1mol, acetone 200ml, to carboxyl essence of Niobe 2mol and Feldalat NM 4mol, stir while leading to nitrogen, it is warmed up to 60 DEG C, 20% sodium hydroxide solution 620g is instilled with 60min, keep 60 DEG C of temperature, stirring reaction 15 hours.After reaction, with the impurity in physical method removal system and moisture, distill solvent in system, obtain the carboxylate B1mol that ester equivalent is 160g/eq of said structure.
The compound C obtained is carried out proton nmr spectra sign, and result is as follows:
1HNMR(CDCl3, 500MHz): 8.18-8.24, (s, 8H, benzene ring hydrogen), 3.88 (m, 6H, the hydrogen of the methyl being connected with ester group), 3.39 (m, 12H, the OCH being connected with phosphorus atoms3)��
The position of infrared spectrum characteristic peak: ester carbonyl group 1730-1740cm-1, the C-O-C1200cm of ester group-1, the characteristic absorption peak 1217cm of P=N key in phosphazene backbone-1, P-N874cm in phosphazene backbone-1, the characteristic absorption peak 1217cm of P=N key in phosphazene backbone-1, P-N874cm in phosphazene backbone-1, the absworption peak 2995.3cm of methyl ether-1, P-O-C key absworption peak 1035cm-1��
Add, as firming agent, o-cresol formaldehyde epoxy resin 100g, the curing accelerator pyridine 0.2g that epoxide equivalent is 200g/eq using above-mentioned carboxylate B80g, prepare composition epoxy resin. Adopting this composition epoxy resin to prepare the standard copper-clad plate sample meeting the standard such as GB, UL, called after b copper-clad plate according to general copper-clad plate production process, the performance of test b copper-clad plate, its result represents in table-1.
Embodiment 3
The structural formula of the present embodiment phosphazene compound with carboxylate is as follows:
Put into hexachlorocyclotriph,sphazene 1mol, acetone 200ml in three mouthfuls of 2000ml glass reactors with agitating device, carboxyl essence of Niobe 3mol and Feldalat NM 3mol is stirred while leading to nitrogen, it is warmed up to 60 DEG C, 20% sodium hydroxide solution 620g is instilled with 60min, keep 60 DEG C of temperature, stirring reaction 15 hours. After reaction, with the impurity in physical method removal system and moisture, distill solvent in system, obtain the carboxylate C1mol that ester equivalent is 140g/eq of said structure.
The compound C obtained is carried out proton nmr spectra sign, and result is as follows:
1HNMR(CDCl3,500MHz):3.39(m,15H,OCH3), 7.80, (s, 2H, the hydrogen on the phenyl of ester group ortho position), 6.84 (m, 2H, the hydrogen on the phenyl of position between ester group), 3.88 (m, 3H, the hydrogen of the methyl being connected with ester group).
The position of infrared spectrum characteristic peak: ester carbonyl group 1730-1740cm-1, the C-O-C1200cm of ester group-1, the characteristic absorption peak 1217cm of P=N key in phosphazene backbone-1, P-N874cm in phosphazene backbone-1, the characteristic absorption peak 1217cm of P=N key in phosphazene backbone-1, P-N874cm in phosphazene backbone-1, the absworption peak 2995.3cm of methyl ether-1, P-O-C key absworption peak 1035cm-1��
Add, as firming agent, o-cresol formaldehyde epoxy resin 100g, the curing accelerator pyridine 0.2g that epoxide equivalent is 200g/eq using above-mentioned carboxylate C70g, prepare composition epoxy resin. Adopting this composition epoxy resin to prepare the standard copper-clad plate sample meeting the standard such as GB, UL, called after c copper-clad plate according to general copper-clad plate production process, the performance of test c copper-clad plate, its result represents in table-1.
Comparative example 1
Epoxide equivalent is the o-cresol formaldehyde epoxy resin 200g of 200g/eq, add the pyridine of linear phenol-aldehyde resin firming agent 105g that phenolic hydroxyl equivalent is 105g/eq and six phenoxy group phosphorus cyanogen 70g and 0.2g as fire retardant, it is dissolved into solution with appropriate butanone, use normal glass cloth, manufacture method conventionally, obtaining the copper-clad plate d that resinous amount is 50%, the properties covering copper d represents in table-1.
Comparative example 2
Epoxide equivalent is the o-cresol formaldehyde epoxy resin 200g of 200g/eq, adding has such as the resin compound 220g of formula (1) structure, ester equivalent is 220g/eq and the pyridine of six phenoxy group phosphorus cyanogen 70g and the 0.2g as fire retardant, it is dissolved into solution with appropriate butanone, use normal glass cloth, manufacture method conventionally, obtains the copper-clad plate e that resinous amount is 50%.The properties covering copper e represents in table-1.
The test result of embodiment and comparative example is such as shown in following table-1 (in view of concrete method of testing is well known to those skilled in the art, at this, method is no longer described in detail).
Table-1
As can be seen from Table 1, the present invention adopts the resin combination that the compound containing the molecular structure shown in formula I is prepared as firming agent, the dielectric constant (1GHz) making the copper-clad plate prepared by it is 3.0-3.1, dielectric loss (1GHz) is 0.004-0.006, Tg can reach 170 DEG C and more than, T-peel strength can reach 1.90kg/mm2And more than, interlaminar strength can reach 1.63kg/mm2And more than, saturated water absorption can reach less than 0.35%, hence it is evident that is better than the performance of comparative example copper-clad plate.
Applicant states, the present invention by above-described embodiment illustrate the present invention with the phosphazene compound of carboxylate, pre-impregnated sheet, composite metal substrate and wiring board, but the invention is not limited in above-described embodiment, namely do not mean that the present invention has to rely on above-described embodiment and could implement. The equivalence of each raw material of product of the present invention, it will be clearly understood that any improvement in the present invention, is replaced and the interpolation of auxiliary element, concrete way choice etc. by person of ordinary skill in the field, all falls within protection scope of the present invention and open scope.
Claims (10)
1. the phosphazene compound with carboxylate, it is characterised in that it has the molecular structure as shown in formula I:
In formula I, R1Representing arbitrary organic group, Y is arbitrary organic group, and R is inertia end-capping group; M is ring three phosphonitrile base M1, ring more than four phosphonitrile base M2Or non-annularity polyphosphazene base M3In the combination of any one or its at least two;
A is the integer be more than or equal to zero, and c is the integer be more than or equal to 1, and a and c sum is equal in M group 2 times of number of phosphorus atoms.
2. phosphazene compound as claimed in claim 1, it is characterised in that R1Represent the combination of any one or its at least two in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
Preferably, the combination of any one or at least two that Y is selected from group:
-O-R2-��-OOC-R3-or
Wherein, R2��R3And R4Combination independently selected from any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or at least two;
Preferably, R is selected from-OR13��-C��C-R18��R22-COO-��OrIn the combination of any one or at least two;
R13For the combination of any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryloxy alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl or at least two, R15��R16And R17All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, R18For the combination of any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl or at least two, R22For any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R23And R24All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, R26And R27All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkoxyl, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted cycloalkyloxy, substituted or unsubstituted aralkoxy, substituted or unsubstituted alkyl-aryloxy, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, R27For any one in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
Preferably, the combination of any one or at least two that Y is selected from group:
R4The combination of any one or at least two in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;
R5��R6And R9All independently be in substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one;
R7And R8All independently be in H, substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, and R7And R8It is asynchronously H;
R10��R11And R12All independently be in H, substituted or unsubstituted straight chained alkyl or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl any one, and R10��R11And R12In at most have two for H;
Preferably, M1Structure is:
M2Structure is:
Wherein, x is be more than or equal to 4;
M3Structure is:
Wherein, y is be more than or equal to 3.
3. the preparation method of the phosphazene compound with carboxylate as claimed in claim 1 or 2, it is characterised in that phosphonitrile chloride and nucleopilic reagent are carried out nucleophilic substitution obtained.
4. a composition epoxy resin, it is characterised in that comprise the phosphazene compound with carboxylate described in claim 1 or 2.
5. a pre-impregnated sheet, it is characterised in that it is impregnated with or coats base material by composition epoxy resin as claimed in claim 4 and forms.
6. pre-impregnated sheet as claimed in claim 5, it is characterised in that described base material is fiberglass substrate, polyester base material, polyimide base material, ceramic base material or carbon fiber base material.
7. a composite metal substrate, it is characterised in that it includes, and more than one pre-impregnated sheet as described in claim 5 or 6 is sequentially carried out surface metal-clad, overlap, pressing form.
8. composite metal substrate as claimed in claim 7, it is characterised in that the alloy that material is aluminum, copper, ferrum and combination in any thereof of described surface metal-clad;
Preferably, described composite metal substrate is CEM-1 copper-clad plate, CEM-3 copper-clad plate, FR-4 copper-clad plate, FR-5 copper-clad plate, CEM-1 aluminium base, CEM-3 aluminium base, FR-4 aluminium base or FR-5 aluminium base.
9. a flexible copper-clad plate, it is characterised in that described flexible copper-clad plate comprises more than one Copper Foil of pre-impregnated sheet and the pre-impregnated sheet one or both sides after being overlying on overlapping as described in claim 5 or 6.
10. a wiring board, it is characterised in that the Surface Machining circuit in the composite metal substrate described in claim 7 or 8 forms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610029549.2A CN105646588A (en) | 2016-01-14 | 2016-01-14 | Phosphazene compound with carboxylic ester, presoaked plate, composite metal substrate and circuit board |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610029549.2A CN105646588A (en) | 2016-01-14 | 2016-01-14 | Phosphazene compound with carboxylic ester, presoaked plate, composite metal substrate and circuit board |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105646588A true CN105646588A (en) | 2016-06-08 |
Family
ID=56487455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610029549.2A Pending CN105646588A (en) | 2016-01-14 | 2016-01-14 | Phosphazene compound with carboxylic ester, presoaked plate, composite metal substrate and circuit board |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105646588A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107522900A (en) * | 2016-06-21 | 2017-12-29 | 广东广山新材料股份有限公司 | Phosphazene compound, plastic packaging material and composite metal substrate with azo group |
| CN107522802A (en) * | 2016-06-21 | 2017-12-29 | 广东广山新材料股份有限公司 | The polycthylene grafted phosphazene compound and hydrogel patch of carboxyl or sulfonic group end-blocking |
| CN107629607A (en) * | 2016-07-05 | 2018-01-26 | 广东广山新材料股份有限公司 | A kind of fireproof coating |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191715A (en) * | 1978-07-03 | 1980-03-04 | Monsanto Company | Flame retarding compound |
| CN102503982A (en) * | 2011-10-31 | 2012-06-20 | 华中师范大学 | Phosphonitrilic chloride trimer epoxy compound with flame-retardant property and preparation and application thereof |
| JP2012177777A (en) * | 2011-02-25 | 2012-09-13 | Fujifilm Corp | Photosensitive composition, photosensitive film, photosensitive laminate, permanent pattern formation method and printed substrate |
| JP2015205990A (en) * | 2014-04-21 | 2015-11-19 | 国立大学法人愛媛大学 | Flame-retardant polymer, production method thereof, and flame-retardant monomer |
| CN105153234A (en) * | 2014-06-13 | 2015-12-16 | 广东生益科技股份有限公司 | A kind of phenoxycyclotriphosphazene active ester, halogen-free resin composition and its application |
-
2016
- 2016-01-14 CN CN201610029549.2A patent/CN105646588A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191715A (en) * | 1978-07-03 | 1980-03-04 | Monsanto Company | Flame retarding compound |
| JP2012177777A (en) * | 2011-02-25 | 2012-09-13 | Fujifilm Corp | Photosensitive composition, photosensitive film, photosensitive laminate, permanent pattern formation method and printed substrate |
| CN102503982A (en) * | 2011-10-31 | 2012-06-20 | 华中师范大学 | Phosphonitrilic chloride trimer epoxy compound with flame-retardant property and preparation and application thereof |
| JP2015205990A (en) * | 2014-04-21 | 2015-11-19 | 国立大学法人愛媛大学 | Flame-retardant polymer, production method thereof, and flame-retardant monomer |
| CN105153234A (en) * | 2014-06-13 | 2015-12-16 | 广东生益科技股份有限公司 | A kind of phenoxycyclotriphosphazene active ester, halogen-free resin composition and its application |
Non-Patent Citations (5)
| Title |
|---|
| CHENG FENG YE等: ""A Novel Synthesis of Some Hexasubstituted Cyclotriphosphazenes"", 《CHINESE CHEMICAL LETTERS》 * |
| DHEERAJ KUMAR等: ""Chiral multidentate oxazolinel igands based on cyclophosphazene cores: synthesis, characterization and complexation studies"", 《DALTON TRANSACTIONS》 * |
| S. LANOUX等: ""REACTIONS OF THE HYDROLYZED PHOSPHAZENE N3P3(OCH2CF3)5ONa"", 《PHOSPHORUS AND SULFUR AND THE RELATED ELEMENTS》 * |
| 胡玉明 等编著: "《固化剂》", 30 April 2004 * |
| 钱立军 等编著: "《新型阻燃剂制造与应用》", 31 March 2013 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107522900A (en) * | 2016-06-21 | 2017-12-29 | 广东广山新材料股份有限公司 | Phosphazene compound, plastic packaging material and composite metal substrate with azo group |
| CN107522802A (en) * | 2016-06-21 | 2017-12-29 | 广东广山新材料股份有限公司 | The polycthylene grafted phosphazene compound and hydrogel patch of carboxyl or sulfonic group end-blocking |
| CN107629607A (en) * | 2016-07-05 | 2018-01-26 | 广东广山新材料股份有限公司 | A kind of fireproof coating |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6318191B2 (en) | Flame retardant compounds, curing agents and polyphenolic epoxy resins | |
| KR101830511B1 (en) | Epoxy resin hardeners and prepatation method and the use thereof | |
| CN105646862B (en) | Polyester, pre-impregnated sheet, composite metal substrate and wiring board containing phosphonitrile | |
| CN106916281A (en) | Flame-retardant compound, curing agent and polyphenol base epoxy | |
| CN105646588A (en) | Phosphazene compound with carboxylic ester, presoaked plate, composite metal substrate and circuit board | |
| US10233204B2 (en) | Phosphazene compound, and a composition, a prepreg and a wiring board comprising the same | |
| CN107337696A (en) | Phosphazene compound, curing agent, phosphonitrile epoxy resin and composite metal substrate and plastic packaging material with aldehyde radical | |
| CN104892906B (en) | The curing agent and epoxy composite of the phosphorus-nitrogen compound of phenolic group containing single aromatic ring | |
| CN107337697A (en) | Phosphazene compound, plastic packaging material and the composite metal substrate of the base containing DOPO | |
| CN106939019A (en) | A kind of phosphazene compound, pre-impregnated sheet, composite metal substrate and wiring board | |
| CN106939016A (en) | A kind of phosphazene compound, pre-impregnated sheet, composite metal substrate and wiring board | |
| CN106939020A (en) | A kind of phosphazene compound, pre-impregnated sheet and composite metal substrate | |
| CN106939017A (en) | A kind of phosphazene compound, pre-impregnated sheet, composite metal substrate and wiring board | |
| CN106939021A (en) | A kind of phosphazene compound, pre-impregnated sheet, composite metal substrate and wiring board | |
| CN107573486A (en) | Sulfydryl phosphazene compound, curing agent and sulfydryl phosphonitrile epoxy resin | |
| CN107573648A (en) | Reactive phosphorus nitrile compound, curing agent and the sulfur-bearing phosphonitrile epoxy resin of sulfur-bearing | |
| CN107337693A (en) | Phosphazene compound, plastic packaging material and composite metal substrate containing phosphinate | |
| CN108250674A (en) | A kind of halogen-free epoxy resin composition and use its prepreg and laminate | |
| CN106939022A (en) | A kind of phosphazene compound, pre-impregnated sheet and composite metal substrate | |
| CN106939018A (en) | A kind of phosphazene compound, pre-impregnated sheet and composite metal substrate | |
| CN107573382A (en) | Non-reacted phosphazene compound, plastic packaging material and the composite metal substrate of sulfur-bearing | |
| JPH0315927B2 (en) | ||
| CN107337806A (en) | Phosphazene compound, plastic packaging material and composite metal substrate containing phosphonate group | |
| CN107573487A (en) | Phosphazene compound containing sulfydryl, curing agent and the epoxy resin of phosphonitrile containing sulfydryl | |
| CN107344975A (en) | A kind of phosphazene compound containing polyacetylene, composition epoxy resin, plastic packaging material and composite metal substrate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information | ||
| CB02 | Change of applicant information |
Address after: 523000 Dongguan Port Road, Guangdong (Sha Tianduan) Humen port service center, Humen port service building on the third floor Applicant after: Guangdong Guang Shan new materials Limited by Share Ltd Address before: 523990 Dongguan Port Road, Guangdong (Sha Tianduan) Humen port service center, Humen port service building 3F Applicant before: GUANG SHAN NEW MATERIALS CO., LTD. |
|
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160608 |