CN108117633B - A kind of compositions of thermosetting resin - Google Patents
A kind of compositions of thermosetting resin Download PDFInfo
- Publication number
- CN108117633B CN108117633B CN201611080924.2A CN201611080924A CN108117633B CN 108117633 B CN108117633 B CN 108117633B CN 201611080924 A CN201611080924 A CN 201611080924A CN 108117633 B CN108117633 B CN 108117633B
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- CN
- China
- Prior art keywords
- resin
- compositions
- thermosetting resin
- curing agent
- epoxy resin
- 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.)
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- 229920005989 resin Polymers 0.000 title claims abstract description 85
- 239000011347 resin Substances 0.000 title claims abstract description 85
- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 53
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 239000011888 foil Substances 0.000 claims abstract description 6
- 239000003822 epoxy resin Substances 0.000 claims description 64
- 229920000647 polyepoxide Polymers 0.000 claims description 64
- 239000003795 chemical substances by application Substances 0.000 claims description 41
- 239000003063 flame retardant Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 15
- 229920001568 phenolic resin Polymers 0.000 claims description 15
- 239000005011 phenolic resin Substances 0.000 claims description 15
- 239000004643 cyanate ester Substances 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 8
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 238000000034 method Methods 0.000 abstract description 12
- 238000010521 absorption reaction Methods 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 4
- -1 brominated Chemical class 0.000 description 41
- 238000001723 curing Methods 0.000 description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 16
- 150000008065 acid anhydrides Chemical class 0.000 description 15
- 239000003205 fragrance Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000004744 fabric Substances 0.000 description 10
- 238000007789 sealing Methods 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000000805 composite resin Substances 0.000 description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000004843 novolac epoxy resin Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000012779 reinforcing material Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 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 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JNCRKOQSRHDNIO-UHFFFAOYSA-N [4-[(4-cyanato-3,5-dimethylphenyl)methyl]-2,6-dimethylphenyl] cyanate Chemical compound CC1=C(OC#N)C(C)=CC(CC=2C=C(C)C(OC#N)=C(C)C=2)=C1 JNCRKOQSRHDNIO-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000009172 bursting Effects 0.000 description 3
- 238000005213 imbibition Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical class O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000000979 retarding effect Effects 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical class OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 229910052755 nonmetal Inorganic materials 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical class CCOCCOC(C)=O SVONRAPFKPVNKG-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
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- ZJWJPEGZUSSHRV-UHFFFAOYSA-N 2-piperidin-1-ylbenzene-1,4-diamine Chemical class NC1=CC=C(N)C(N2CCCCC2)=C1 ZJWJPEGZUSSHRV-UHFFFAOYSA-N 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- ZDCFJCRHWNSQOL-UHFFFAOYSA-N 3-methylpiperidin-2-amine Chemical compound CC1CCCNC1N ZDCFJCRHWNSQOL-UHFFFAOYSA-N 0.000 description 1
- HPCNNXRVKBZCDW-UHFFFAOYSA-N 3-nitropiperidin-2-amine Chemical class NC1NCCCC1[N+]([O-])=O HPCNNXRVKBZCDW-UHFFFAOYSA-N 0.000 description 1
- VWSGKVYQLVXORK-UHFFFAOYSA-N 3-piperidin-1-ylbenzene-1,2-diamine Chemical class NC1=CC=CC(N2CCCCC2)=C1N VWSGKVYQLVXORK-UHFFFAOYSA-N 0.000 description 1
- OYRZFURJZQGZDP-UHFFFAOYSA-N 4,4-dimethylpiperidin-2-amine Chemical compound NC1NCCC(C1)(C)C OYRZFURJZQGZDP-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- UHDGDGPBCVFSDJ-UHFFFAOYSA-N 4-methylpiperidin-2-amine Chemical compound CC1CCNC(N)C1 UHDGDGPBCVFSDJ-UHFFFAOYSA-N 0.000 description 1
- HKQPBNQSLPIIBZ-UHFFFAOYSA-N 5-nitropiperidin-2-amine Chemical class NC1CCC([N+]([O-])=O)CN1 HKQPBNQSLPIIBZ-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910017083 AlN Inorganic materials 0.000 description 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- 241001120493 Arene Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SIZDMAYTWUINIG-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)C1=CC=C(OC#N)C=C1 SIZDMAYTWUINIG-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GMGLYSIINJPYLI-UHFFFAOYSA-N butan-2-one;propan-2-one Chemical compound CC(C)=O.CCC(C)=O GMGLYSIINJPYLI-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 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
- 239000000049 pigment Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- ADJMNWKZSCQHPS-UHFFFAOYSA-L zinc;6-methylheptanoate Chemical compound [Zn+2].CC(C)CCCCC([O-])=O.CC(C)CCCCC([O-])=O ADJMNWKZSCQHPS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08G59/423—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof containing an atom other than oxygen belonging to a functional groups to C08G59/42, carbon and hydrogen
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
- B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
- B32B2307/204—Di-electric
-
- 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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
-
- 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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
- B32B2307/3065—Flame resistant or retardant, fire resistant or retardant
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/22—Halogen free composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
The present invention provides a kind of compositions of thermosetting resin, it includes phosphorous acid anhydrides, the compositions of thermosetting resin has good thermal stability, humidity resistance, toughness, dielectric constant and the advantages that dielectric loss angle tangent is low, water absorption rate is low and halogen-free flameproof effect, and there is excellent technique processability；The present invention also provides application of the compositions of thermosetting resin in resin sheet, resin laminated metal foil, prepreg, laminate, metal-clad laminate and printed wiring board.
Description
Technical field
The present invention relates to technical field of polymer materials more particularly to a kind of compositions of thermosetting resin and use the pre- of it
Leaching material and laminate for printed circuits.
Background technique
It is fire-retardant to realize that traditional laminate for printed circuits generallys use bromide fire retardant, especially with tetrabromobisphenol
A type epoxy resin, this brominated epoxy resin has good anti-flammability, but it can generate bromination hydrogen in burning.This
Outside, dioxin, dibenzo have been detected in the combustion product of the waste electrical and electronic equipment of the halogens such as brominated, chlorine in recent years
The carcinogens such as furans, therefore the application of brominated epoxy resin is restricted.On July 1st, 2006, two parts of environmental protection instructions of European Union
" about electric/electronic device instruction is scrapped " and " Restriction on the Use of Certain Hazardous Substances in Electrical and Electronic Equipment " is just
Formula is implemented, and the hot spot for being developed into industry of halogen-free flameproof copper-clad laminate, each copper-clad laminate producer all releases one after another
The halogen-free flameproof copper-clad laminate of oneself.
Phosphorus-containing compound is introduced in the resin matrix of copper-clad plate, becomes the main technological route of copper-clad plate halogen-free flameproof.
The phosphonium flame retardant being widely used on copper-clad plate field at present is broadly divided into response type and two kinds of addition type.Response type is mainly
DOPO class compound, based on phosphorous epoxy resin, phosphorus containing phenolic resin, phosphorus content is between 2%~10%.However, practical
It is found in, DOPO class compound has biggish water absorption rate and poor dielectric properties and plate humidity resistance poor.Addition
Type is mainly phosphonitrile and phosphonate ester compound, and the flame retarding efficiency of additive flame retardant is lower, needs to add more amount ability
Reach flame-retardancy requirements.It is easy to migrate to plate in laminate process simultaneously because of its lower fusing point (generally below 150 DEG C)
Material surface, influences plate property.
In addition, for copper clad foil substrate material, in order to meet the performance of PCB processing performance and terminal electronic product
It is required that, it is necessary to have good dielectric properties, heat resistance and mechanical performance, while should also have good technique processing special
Property, high peel strength, excellent humidity resistance and UL94 V-0 halogen-free flameproof rank.
End oxybenzene oxygroup alkyl phosphine oxide is the phosphorus curing agent with reactivity, can be cured with epoxy resin instead
It answers, but since its active group is phenolic hydroxyl group, the biggish secondary hydroxyl of polarity can be generated after reacting with epoxy resin, is caused
The dielectric properties of solidfied material are poor.Selecting in CN103384674A has the polyphosphonates of hydroxyl or/and phosphonate ester-carbonic ester total
Polymers and epoxy form composition, and active group is phenolic hydroxyl group, equally exist the poor problem of dielectric properties；
Disclosed in CN103694642A using epoxy resin, cyanate esters or/and cyanate prepolymer, polyphosphonates or/and
Phosphonate ester-carbonate copolymer is prepared for the good fire-retardant prepreg of Halogen UL94 V-0 of dielectric properties, humidity resistance and covers copper
Foil laminate, but its peel strength, interlayer adhesion and bending strength are lower.
Summary of the invention
Through inventor the study found that with phosphorous acid anhydrides, i.e., double hydroxyl fragrance oxygroup alkyl phosphine oxides of acid anhydrides sealing end are as ring
The curing agent of oxygen resin will not generate the big secondary hydroxyl of polarity, keep the dielectric properties of system preferable when reacting with epoxy resin,
Simultaneously because itself be phosphorous active curing agent, the effect of there are also halogen-free flameproofs while being used as curing agent, need to only lack
Amount addition can make plate achieve the effect that UL94 V-0 halogen-free flameproof without adding other fire retardants just.
Based on this, one of the objects of the present invention is to provide a kind of compositions of thermosetting resin, and use its preimpregnation
Material and laminate for printed circuits.There is high glass transition temperature using the laminate for printed circuits that the resin combination makes
Degree, excellent dielectric properties, high-fire resistance and good technique processability, and it is able to achieve halogen-free flameproof, reach UL94 V-0.
The present inventor to achieve the above object, has carried out in-depth study repeatedly, as a result, it has been found that: by halogen-free epoxy resin,
Double hydroxyl fragrance oxygroup alkyl phosphine oxides of acid anhydrides sealing end and the composition that optionally other curing agent properly mix, can reach
Above-mentioned purpose.
That is, the present invention adopts the following technical scheme: a kind of compositions of thermosetting resin, it includes epoxy resin and solidifications
Agent, wherein curing agent includes at least a kind of phosphorous acid anhydrides, i.e. double hydroxyl fragrance oxygroup alkyl phosphine oxides of acid anhydrides sealing end.
Compositions of thermosetting resin of the invention is using double hydroxyl fragrance oxygroup alkyl phosphine oxides of acid anhydrides as epoxy resin
Curing agent.It is wherein high as the active ester groups content of active group, can with to obtain crosslink density after epoxy resin cure big
Solidfied material, available heat-resist, Tg high material；And double hydroxyl fragrance oxygroup alkyl phosphine oxide structures pair of acid anhydrides
Title property is high, and the active ester units in molecule reacted with epoxy resin after will not generate the secondary hydroxyl of polarity greatly, can eliminate
The shortcomings that polarity big secondary hydroxyl bring poor dielectric performance, keep dielectric properties excellent；Double hydroxyl fragrance oxygen of the acid anhydrides
Base alkyl phosphine oxide is active ester, its water absorption rate of the ester bond generated after reacting with epoxy resin is low, makes which improve phosphorous chemical combination
The disadvantage of object humidity resistance difference.In addition, double hydroxyl fragrance oxygroup alkyl phosphine oxides of acid anhydrides can have the effect of halogen-free flameproof, only
It need to add on a small quantity or can to reach UL94 V-0 fire-retardant without additionally adding fire retardant.
The present invention, can be significant using the active ester group of double hydroxyl fragrance oxygroup alkyl phosphine oxides of high symmetrical acid anhydrides
The glass transition temperature and heat resistance of the prepreg and laminate for printed circuits that make using the resin combination are improved,
And excellent dielectric properties, low water absorption, good humidity resistance and good technique processability are made it have, and realize Halogen
It is fire-retardant, reach UL94 V-0.Each component is described in detail below.
According to the present invention, shown in the structural formula such as formula (I) of the phosphorous acid anhydrides:
Wherein, R1ForNaphthalene, containing carbon number be 1~4 linear or branched alkyl group in any one；Its
In the linear or branched alkyl group containing carbon number 1~4 for example can be methyl, ethyl, propyl, butyl, isopropyl, isobutyl group or tertiary fourth
Any one in base；
Wherein, n1For 0~5 integer, such as 0,1,2,3,4 or 5；
Wherein, R3For be 1~4 containing carbon number linear or branched alkyl group in any one；Wherein containing the straight of carbon number 1~4
Chain or branched alkyl for example can be any one in methyl, ethyl, propyl, butyl, isopropyl, isobutyl group or tert-butyl；
Wherein, R2Any one in following group:
Wherein, any one of Ar in following group:
Double hydroxyl fragrance oxygroup alkyl phosphine oxides of acid anhydrides sealing end in the present invention, structural formula can be such as flowering structure:
According to the present invention, the phosphorous acid anhydrides accounts for epoxy resin and curing agent total weight in the compositions of thermosetting resin
20%~60%, such as 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 35%, 38%, 40%, 42%,
45%, the specific point value between 48%, 50%, 52%, 55%, 58% or 60% and above-mentioned numerical value, as space is limited and for
Concise consideration, the specific point value that range described in the present invention no longer exclusive list includes.
In the present invention, the phosphorous acid anhydrides preferably accounts for epoxy resin and curing agent gross weight in the compositions of thermosetting resin
The 20%~45% of amount, further preferred 25%~40%, still more preferably 25%~30%.
According to the present invention, the epoxy resin accounts for epoxy resin and curing agent total weight in the compositions of thermosetting resin
30%~60%, such as 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 45%, 48%, 50%, 52%,
55%, the specific point value between 58% or 60% and above-mentioned numerical value, as space is limited and for concise consideration, the present invention is not
The specific point value that range described in exclusive list includes again.
Present invention preferably employs halogen-free epoxy resin, the halogen-free epoxy resin refer in 1 molecule tool there are two or
The epoxy resin of more than two epoxy groups can specifically be selected from glycidol ethers, glycidol esters, glycidyl amine
In class, cycloaliphatic epoxy resin, epoxidation of olefins class, glycolylurea epoxide resin or acid imide epoxy resin any one or at least
Two kinds of mixture, wherein typical but non-limiting mixture are as follows: glycidol ethers and glycidol esters, aliphatic ring
Oxygen resin and epoxidation of olefins class, glycidol amine and glycolylurea epoxide resin.
Preferably, the glycidol ethers include bisphenol A type epoxy resin, bisphenol f type epoxy resin, o-cresol phenolic aldehyde
Epoxy resin, bisphenol A-type novolac epoxy resin, three phenolic novolac epoxy resins, dicyclopentadiene novolac epoxy resin, biphenyl type
Any one in novolac epoxy resin, alkyl benzene-type novolac epoxy resin or naphthol type novolac epoxy resin or at least two
Mixture.
It is further preferred that the glycidol ethers are selected from the epoxy resin having the following structure:
Wherein, Z1、Z2And Z3It is each independently selected fromR4Selected from hydrogen atom, replace
Or any one in unsubstituted straight chained alkyl or branched alkyl containing carbon number 1~5；Such as it can be methyl, ethyl, third
Any one in base, butyl, amyl, isopropyl, isobutyl group, tert-butyl or isopentyl；
Wherein, Y1And Y2It is each independently selected from-CH2-、 In any one；R5Selected from hydrogen original
Any one in sub, substituted or unsubstituted straight chained alkyl or branched alkyl containing carbon number 1~5；Such as it can be methyl, second
Any one in base, propyl, butyl, amyl, isopropyl, isobutyl group, tert-butyl or isopentyl；
Wherein, n2For 1~10 arbitrary integer, such as 1,2,3,4,5,6,7,8,9 or 10.
Preferably, it is different to be selected from triglycidyl group-p- amino-phenol, triglycidyl group trimerization for the glycidol amine
Cyanate, four glycidyl group diamino dimethylene benzene, four glycidyl group -4,4 '-diaminodiphenylmethane, four shrinks are sweet
Oil base -3,4 '-diaminodiphenyl ether, four glycidyl group -4,4 '-diaminodiphenyl ether or four glycidyl group -1,3- diamino
In ylmethyl hexamethylene any one or at least two mixture.
Halogen-free thermosetting resin composite of the invention uses the halogen-free epoxy resin of above-mentioned specific molecular structure, has
Higher degree of functionality and good dielectric properties, solidfied material Tg higher, water absorption rate are low.
According to the present invention, the thermal curing agents can also include cyanate ester resin and/or bismaleimide-triazine tree
Rouge；Wherein, the cyanate ester resin has the following structure:
Wherein, R14For-CH2-、
In any one or at least two mixture；R6、R7、R8、R9、R10、R11、R12、R13It is each independently selected from hydrogen atom, takes
Any one in generation or unsubstituted straight chained alkyl or branched alkyl containing carbon number 1~4, such as can be methyl, ethyl, third
Any one in base, butyl, isopropyl, isobutyl group or tert-butyl.
Preferably, the cyanate ester resin is selected from bis- (the 4- cyanato- phenyl) propane of 2,2-, bis- (4- cyanato- phenyl) second
Alkane, bis- (3,5- dimethyl -4- cyanato- phenyl) methane, bis- (4- cyanato- the phenyl) -1,1,1,3,3,3- hexafluoropropane of 2,2-,
Bis- (4- cyanato- the phenyl)-diisopropyl benzenes of α, α '-, Cyclopeutadiene type cyanate, phenol novolak type cyanate, cresol novolac
Bis- (4- cyanato- phenyl) the propane prepolymers of type cyanate, 2,2-, bis- (4- cyanato- phenyl) ethane prepolymers, bis- (3,5- bis-
Methyl -4- cyanato- phenyl) methane prepolymer, bis- (4- cyanato- the phenyl) -1,1,1,3,3,3- hexafluoropropane prepolymers of 2,2-,
Bis- (4- cyanato- the phenyl)-diisopropyl benzene prepolymers, dicyclopentadiene type ethylene rhodanate prepolymer, phenol novolak type of α, α '-
In cyanate prepolymer or cresol novolak type cyanate prepolymer any one or at least two mixture, preferably 2,2-
Bis- (4- cyanato- phenyl) propane, α, bis- (4- cyanato- the phenyl)-diisopropyl benzenes of α ' -, bis- (3,5- dimethyl -4- cyanogen oxygen
Base phenyl) methane, 2,2- bis- (4- cyanato- phenyl) propane prepolymers, α, bis- (4- cyanato- the phenyl)-diisopropyl benzenes of α '-
In prepolymer or bis- (3,5- dimethyl -4- cyanato- phenyl) methane prepolymers any one or at least two mixture.
According to the present invention, the cyanate ester resin and/or bismaleimide-triazine resin account for the thermosetting resin group
Close 0%~50% of epoxy resin and curing agent total weight in object, for example, 0%, 2%, 4%, 5%, 8%, 10%, 12%,
14%, 15%, 17%, 20%, 22%, 25%, 30%, 32%, 35%, 37%, 39%, 40%, 42%, 45%, 48% or
Specific point value between 50% and above-mentioned numerical value, as space is limited and for concise consideration, the present invention no longer exclusive list institute
State the specific point value that range includes.
According to the present invention, the curing agent can also include SMA resin；The SMA resin means phenylethylene-maleic anhydride
Resin can use and be copolymerized to obtain in the ratio of 1:1~8:1 by styrene and maleic anhydride.
According to the present invention, the SMA resin accounts for epoxy resin and curing agent total weight in the compositions of thermosetting resin
0%~40%, such as 0%, 2%, 4%, 5%, 8%, 10%, 12%, 14%, 15%, 17%, 20%, 22%, 25%,
30%, the specific point value between 32%, 35%, 37%, 39% or 40% and above-mentioned numerical value, as space is limited and for simplicity
The considerations of, specific point value that range described in the present invention no longer exclusive list includes.
According to the present invention, the curing agent can also include phenolic resin；The phenolic resin is phosphorous or not phosphorous
Phenolic resin, is phenolic resin well known in the art, and the present invention does not do particular determination.
According to the present invention, the phenolic resin accounts for epoxy resin and curing agent total weight in the compositions of thermosetting resin
0%~20%, such as 0%, 2%, 4%, 5%, 8%, 10%, 12%, 14%, 15%, 17% or 20% and above-mentioned number
Specific point value between value, as space is limited and for concise consideration, the tool that range described in the present invention no longer exclusive list includes
Body point value.
Heretofore described compositions of thermosetting resin, organic solid content specifically include based on 100 parts by weight: acid anhydrides
Double hydroxyl fragrance oxygroup alkyl phosphine oxides of sealing end: 20~60 parts by weight；Halogen-free epoxy resin: 30~60 parts by weight；Cyanate resin
Rouge and/or bismaleimide-triazine resin: 0~50 parts by weight；SMA resin: 0~40 parts by weight；Phenolic resin: 0~20 weight
Measure part.
" epoxy resin and curing agent total weight in the compositions of thermosetting resin " mentioned in the present invention refers to ginseng
With the total weight of the component of cross-linking polymerization, wherein curing agent refers to the acid anhydrides sealing end for playing the role of cured epoxy resin
Double hydroxyl fragrance oxygroup alkyl phosphine oxides and optionally cyanate ester resin and/or bismaleimide-triazine resin, SMA resin
Or phenolic resin, do not include the components such as filler, promotor and fire retardant.
Compositions of thermosetting resin of the invention can also include organic halogen-free flame retardants, can specifically be selected from phosphor-containing flame-proof
Agent.
According to the present invention, the phosphonium flame retardant is selected from three (2,6- 3,5-dimethylphenyl) phosphines, 10- (2,5- dihydroxy benzenes
Base) miscellaneous -10- phosphine phenanthrene -10- oxide of -9,10- dihydro-9-oxy, 2,6- bis- (2,6- 3,5-dimethylphenyl) phosphino- benzene, 10- phenyl -
Miscellaneous -10- phosphine phenanthrene -10- the oxide of 9,10- dihydro-9-oxy, phenoxy phosphazene compound, phosphate, polyphosphate, polyphosphonates
In phosphonate ester-carbonate copolymer any one or at least two mixture.
In the present invention, epoxy resin and curing agent total amount in the compositions of thermosetting resin have based on 100 parts by weight
The additive amount of machine halogen-free flame retardants is 0~15 parts by weight, that is to say, that is aoxidized by double hydroxyl fragrance oxygroup alkyl of acid anhydrides sealing end
The sum of phosphine, epoxy resin and the cyanate ester resin that may be added, SMA resin, the additive amount of phenolic resin are 100 parts by weight meters,
The additive amount of organic halogen-free agent is 0~15 parts by weight, such as 1 parts by weight, 3 parts by weight, 5 parts by weight, 6 parts by weight, 8 weight
Tool between part, 9 parts by weight, 10 parts by weight, 11 parts by weight, 12 parts by weight, 13 parts by weight or 15 parts by weight and above-mentioned numerical value
Body point value, as space is limited and for concise consideration, the specific point value that range described in the present invention no longer exclusive list includes.
Halogen-free thermosetting resin composite of the invention can also include curing accelerator.
Preferably, the curing accelerator includes organic metal salt and selected from glyoxaline compound, glyoxaline compound
In derivative, piperidines, pyridine compounds and their, lewis acid or triphenylphosphine any one or at least two it is mixed
Close object.
Preferably, the organic metal salt in the curing accelerator includes sad metal salt, isooctyl acid metal salt, levulinic
In ketone metal salt, metal naphthenate, salicylic acid metal salt or Metallic stearates any one or at least two mixing
Object, wherein the metal in zinc, copper, iron, tin, cobalt or aluminium any one or at least two mixture.
Preferably, the glyoxaline compound is 2-methylimidazole, 2-ethyl-4-methylimidazole, 2- phenylimidazole or 2-
In undecyl imidazole any one or at least two mixture.
Preferably, the piperidines are 2,3- diamino phenylpiperidines, 2,5- diamino phenylpiperidines, 2,6- diamino piperazine
Pyridine, 2- amino -3- methyl piperidine, 2- amino -4- methyl piperidine, 2- amino -3- nitro piperidines, 2- amino -5- nitro piperidines or
In 2- amino -4,4- lupetidine any one or at least two mixture.
Preferably, the pyridine compounds and their is 4-dimethylaminopyridine, 2-aminopyridine, 3- aminopyridine or 4- amino
Any one in pyridine or at least two mixtures.
Preferably, added with phosphorous acid anhydrides, epoxy resin and the cyanate ester resin that may be added, SMA resin, phenolic resin
The sum of dosage is 100 parts by weight meters, and the additive amount of the curing accelerator is 0.01~1 parts by weight, such as 0.01 parts by weight,
0.025 parts by weight, 0.05 parts by weight, 0.07 parts by weight, 0.085 parts by weight, 0.1 parts by weight, 0.3 parts by weight, 0.5 parts by weight,
0.8 parts by weight, 0.9 parts by weight or 1 parts by weight, preferably 0.025~0.85 parts by weight.
Halogen-free thermosetting resin composite of the invention can also include filler.
Preferably, the filler is selected from organic filler or inorganic filler, preferably inorganic filler, further preferably by surface
The inorganic filler of processing, most preferably surface treated silica.
Preferably, it is even to be selected from silane coupling agent, silicone oligomer or titanate esters for the surface treating agent of the surface treatment
Join agent in any one or at least two mixture.
Preferably, in terms of by inorganic filler for 100 parts by weight, the dosage of the surface treating agent is 0.1~5 parts by weight, excellent
Select 0.5~3 parts by weight, more preferable 0.75~2 parts by weight.
Preferably, the inorganic filler is selected from nonmetal oxide, metal nitride, non-metal nitride, inorganic hydration
In object, inorganic salts, metal hydrate or Phos any one or at least two mixture, preferred molten silica,
Crystalline sillica, spherical silica, hollow silicon dioxide, aluminium hydroxide, aluminium oxide, talcum powder, aluminium nitride, nitridation
In boron, silicon carbide, barium sulfate, barium titanate, strontium titanates, calcium carbonate, calcium silicates or mica any one or at least two it is mixed
Close object.
Preferably, the organic filler is any one in polytetrafluorethylepowder powder, polyphenylene sulfide or polyether sulfone powder
Kind or at least two mixture.
Preferably, the median of the filler be 0.01~50 μm, preferably 0.01~20 μm, further preferred 0.1~
10μm。
Preferably, added with phosphorous acid anhydrides, epoxy resin and the cyanate ester resin that may be added, SMA resin, phenolic resin
The sum of dosage is 100 parts by weight meters, and the additive amount of the filler is 5~300 parts by weight, preferably 5~200 parts by weight, further
It is preferred that 5~150 parts by weight.
"comprising" of the present invention, it is intended that it can also include other components, these other components especially except described group
Assign the halogen-free thermosetting resin composite different characteristics.In addition to this, "comprising" of the present invention can also replace
For enclosed " for " or " by ... form ".
For example, the halogen-free thermosetting resin composite can also contain various additives, as concrete example, can enumerate
Antioxidant, heat stabilizer, antistatic agent, ultraviolet absorbing agent, pigment, colorant or lubricant etc..These additives can be single
It solely uses, two or more can also be used in mixed way.
The preparation method of halogen-free thermosetting resin composite of the invention is ordinary skill in the art means, specific side
Method are as follows: first solid content is put into, is then added liquid solvent, after stirring is completely dissolved to solid content, add liquid resin and
Promotor continues to stir evenly.
As the solvent in the present invention, there is no particular limitation, as concrete example, can enumerate methanol, ethyl alcohol, butanol
Equal alcohols, the ethers such as ethyl cellosolve, butyl cellosolve, ethylene glycol monomethyl ether, carbitol, butyl carbitol, acetone, butanone, first
The ketones such as methyl ethyl ketone methyl ketone, cyclohexanone；The arenes such as toluene, dimethylbenzene；The esters such as ethyl acetate, ethoxyethyl acetate
Class；The nitrogen-containing solvents such as N,N-dimethylformamide, DMAC N,N' dimethyl acetamide.The above solvent can be used alone, can also be two kinds
Or it two or more is used in mixed way.It is preferred that the ketones such as acetone, butanone, methyl ethyl ketone, cyclohexanone.The additive amount of the solvent by
Those skilled in the art select according to oneself experience, so that resin adhesive liquid reaches the viscosity for being suitble to use.
Prepreg of the invention include reinforcing material and impregnation it is dry after be attached to nothing as described above on reinforcing material
Halogen compositions of thermosetting resin, used reinforcing material are limited without special, can be organic fiber, inorfil woven cloth
Or non-woven fabrics.The organic fiber can choose aramid nonwoven, the inorfil woven cloth can for E- glass-fiber-fabric,
D- glass-fiber-fabric, S- glass-fiber-fabric, T glass-fiber-fabric, NE- glass-fiber-fabric or quartz fabric.The thickness of the reinforcing material is not particularly limited, and is in
Laminate has the considerations of good dimensional stability, the woven cloth and nonwoven thickness preferably 0.01~0.2mm, and preferably
It is surface-treated by fibrillation processing and silane coupling agent, it is described silane coupled in order to provide good water resistance and heat resistance
Agent is preferably any one or at least two in epoxy silane coupling agent, amino silicane coupling agent or vinyl silicane coupling agent
Mixture.By reinforcing material by being impregnated with above-mentioned halogen-free thermosetting resin composite, under the conditions of 100~250 DEG C, baking
Obtain the prepreg within 1~15 minute.
Laminate for printed circuits of the invention includes by being heated and pressurizeed, making the prepreg of a piece of or two panels or more viscous
It is combined and manufactured laminate, and is bonded in the metal foil of laminate one or both sides or more.The laminate is
Solidify in hot press and be made, solidification temperature is 150~250 DEG C, and solidifying pressure is 10~60kg/cm2.The metal foil is
Copper foil, nickel foil, aluminium foil and SUS foil etc., material is unlimited.
Compared with prior art, the present invention at least has the advantages that
Prepreg made of halogen-free thermosetting resin composite provided by the present invention and laminate for printed circuits, have
Up to 215 DEG C of glass transition temperature；Excellent dielectric properties, water absorption rate control in 0.06~0.1% range；High heat resistance
Property；Excellent humidity resistance and good technique processability；Excellent flame retarding efficiency, P content 1.98% can reach UL94
V-0。
Specific embodiment
The technical scheme of the invention is further explained by means of specific implementation.
As described below is the specific embodiment of the embodiment of the present invention, it is noted that for the common skill of the art
For art personnel, without departing from the principles of the embodiments of the present invention, several improvements and modifications can also be made, these improvement
Also it is considered as the protection scope of the embodiment of the present invention with retouching.
Divide multiple embodiments that the embodiment of the present invention is further detailed below.The embodiment of the present invention be not limited to
Under specific embodiment.Do not changing in the scope of the claims, appropriate can change implementation.
1, the synthesis of phosphorous acid anhydrides P-A1
By bis- (4- oxybenzene oxygroup) the methyl oxidation phosphines of 280g, the 1,2,4- Trimellitic Anhydride Chloride and 1500g pyridine of 425g
It is stirred in the four-necked bottle that blender, condensing reflux pipe, thermometer are housed, while being passed through nitrogen, be then warming up to 30 DEG C, herein
At a temperature of react 4h.Product is cooled to room temperature, 5% sodium carbonate liquor is then added, and be vigorously stirred, filtered, washes, dries,
Obtain product, number P-A1.
2, the synthesis of phosphorous acid anhydrides P-A2
By bis- (the 4- hydroxyl biphenylyloxy) phenyl phosphine oxides of 494g, the 1,2,4- Trimellitic Anhydride Chloride and 1500g pyrrole of 425g
Pyridine is stirred in the four-necked bottle that blender, condensing reflux pipe, thermometer are housed, while being passed through nitrogen, is then warming up to 30 DEG C,
4h is reacted at a temperature of this.Product is cooled to room temperature, 5% sodium carbonate liquor is then added, and be vigorously stirred, filtered, washes, does
It is dry, obtain product, number P-A2.
3, the synthesis of phosphorous acid anhydrides P-A3
By 442g bis- -2 (7- hydroxyl naphthoxy) phenyl phosphine oxide, the 1,2,4- Trimellitic Anhydride Chloride and 1500g pyrrole of 425g
Pyridine is stirred in the four-necked bottle that blender, condensing reflux pipe, thermometer are housed, while being passed through nitrogen, is then warming up to 30 DEG C,
4h is reacted at a temperature of this.Product is cooled to room temperature, 5% sodium carbonate liquor is then added, and be vigorously stirred, filtered, washes, does
It is dry, obtain product, number P-A3.
4, the synthesis of phosphorous acid anhydrides P-A4
By bis- (the hydroxyl fluorenes oxygroup) phenyl phosphine oxides of 830g, the 1,2,4- Trimellitic Anhydride Chloride of 425g and 1500g pyridine in
Equipped with blender, condensing reflux pipe, thermometer four-necked bottle in stir, while being passed through nitrogen, be then warming up to 30 DEG C, it is warm herein
Degree is lower to react 4h.Product is cooled to room temperature, 5% sodium carbonate liquor is then added, and be vigorously stirred, filtered, washes, dries, obtain
To product, number P-A4.
5, the synthesis of phosphorous acid anhydrides P-A5
By bis- (3- oxybenzene the oxygroup) -4- aminomethyl phenyl phosphine oxides of 356g, 520g 7- formyl chloro -2,3- naphthoic acid acid anhydride and
1500g pyridine stirs in the four-necked bottle that blender, condensing reflux pipe, thermometer are housed, while being passed through nitrogen, is then warming up to
30 DEG C, 4h is reacted at this temperature.Product is cooled to room temperature, 5% sodium carbonate liquor is then added, and is vigorously stirred, filtering,
Washing, drying, obtain product, number P-A5.
By above-mentioned phosphorous acid anhydrides P-A, halogen-free epoxy resin and curing accelerator, halogen-free flame retardants, filler by certain ratio
Example is uniformly mixed in solvent, and control glue solid content is 65%, impregnates above-mentioned glue with 2116 glass-fiber-fabrics, is controlled suitable thick
Then degree toasts 2~15min in 115~175 DEG C of baking oven and prepreg is made, then stacks several prepregs,
The stacked on 18 μ RTF copper foil in its two sides is 170~250 DEG C in solidification temperature, and solidifying pressure is 25~60kg/cm2, curing time is
Copper-clad plate is made under the conditions of 60~300min.
Embodiment 1~17 and comparative example 1~7 are related to material and trade mark information is as follows:
(A) phosphorous acid anhydrides P-A
P-A1: phosphorous acid anhydrides P-A is made by oneself
P-A2: phosphorous acid anhydrides P-A is made by oneself
P-A3: phosphorous acid anhydrides P-A is made by oneself
P-A4: phosphorous acid anhydrides P-A is made by oneself
P-A5: phosphorous acid anhydrides P-A is made by oneself
BHPPO: bis- (4- oxybenzene oxygroup) phenyl phosphine oxides
FRX-3001:
(B) cyanate
CY-40: Wuqiao resin factory, DCPD type cyanate ester resin
PT-60S:LONCZ, Novolac Cyanate Ester Resins
CE01PS: Jiangsu apocalypse, bisphenol A cyanate ester resin
CE01MO: Jiangsu apocalypse, bisphenol A cyanate ester resin
(C) epoxy resin
HP-7200HHH:DIC, DCPD type epoxy resin, epoxide equivalent 288
HP-7200H-75M:DIC, DCPD type epoxy resin, epoxide equivalent 280
HP-6000:DIC, epoxy resin, epoxide equivalent 250
HP-9900:DIC, naphthol type epoxy resin, epoxide equivalent 274
NC-3000H: Japanese chemical drug, biphenyl epoxy resin, epoxide equivalent 294
SKE-1: Shang Kete, special epoxy resin, epoxide equivalent 120
SKE-3: Shang Kete, special epoxy resin, epoxide equivalent 120
(D) phenolic resin
DOW92741: phosphorus-containing phenolic aldehyde, DOW Chemical
SEB-0904PM60: phosphorus-containing phenolic aldehyde, SHIN-A
SHN-1655TM65: phosphorus-containing phenolic aldehyde, SHIN-A
2812: linear phenolic resin, MOMENTIVE (South Korea)
(E) phosphonium flame retardant
SPB-100: big tomb chemistry, phosphine nitrile fire retardant, phosphorus content 13.4%
(F)SMA
1000P:SMA, Sartomer
EF40:SMA, Sartomer
EF60:SMA, Sartomer
EF80:SMA, Sartomer
(G) promotor
2E4MZ:2- ethyl -4-methylimidazole, four countries' chemical conversion
DMAP:4- dimethylamino naphthyridine, wide Rong Huaxue
BICAT Z: zinc Isoocatanoate, The Shepherd Chemical Company
(H) filler
Fused silica (average grain diameter is 1 to 10 μm, 99% or more purity)
Table 1-4 is embodiment 1~17, and table 5 is the formula composition and its physical data of comparative example 1~7.
Table 1
Table 2
Table 3
| Embodiment 10 | Embodiment 11 | Embodiment 12 | Embodiment 13 | |
| P-A1 | 40 | |||
| P-A2 | 50 | |||
| P-A3 | ||||
| P-A4 | 60 | |||
| P-A5 | 20 | |||
| DOW92741 | 10 | |||
| SEB-0904PM60 | 15 | |||
| SHN-1655TM65 | 20 | |||
| 2812 | 5 | |||
| HP-6000 | 55 | |||
| HP-9900 | ||||
| NC-3000H | 60 | |||
| SKE-1 | 30 | |||
| SKE-3 | 35 | |||
| 2E4MZ | 0.1 | |||
| Ball silicon | 0 | 50 | 100 | 300 |
| P% | 2.58% | 3.34% | 2.17% | 1.98% |
| Tg(DMA)/℃ | 190 | 188 | 180 | 178 |
| Dk(10GHz) | 3.8 | 3.8 | 3.8 | 3.8 |
| Df(10GHz) | 0.0072 | 0.0072 | 0.0078 | 0.0072 |
| Water imbibition/% | 0.08 | 0.08 | 0.075 | 0.08 |
| PCT/6h | OOO | OOO | OOO | OOO |
| T288/min | > 60 | > 60 | > 60 | > 60 |
| Difficult to burn | V-0 | V-0 | V-0 | V-0 |
Table 4
Table 5
PCT/6h performance map target supplementary explanation: × to be layered plate bursting, O is not stratified plate bursting.
The test method of the above characteristic is as follows:
(1) glass transition temperature (Tg): being tested using DMA, is surveyed according to the DMA of IPC-TM-650 2.4.24 defined
Method for testing is measured.
(2) it dielectric constant and dielectric loss factor: is tested according to SPDR method.
(3) humidity resistance (PCT) is evaluated: after the copper foil on copper-clad plate surface is etched, evaluating substrate；By substrate placement force
In pot, after being handled 6 hours under the conditions of 120 DEG C, 105KPa, it is immersed in 288 DEG C of tin furnace, is recorded when substrate de-lamination plate bursting
The corresponding time；It can terminate to evaluate when substrate also does not occur blistering or being layered in tin furnace more than 5min.
(4) T288: TMA instrument is used, is measured according to the T300 test method of IPC-TM-650 2.4.24.1 defined.
(5) it water imbibition: is measured according to the water imbibition test method of IPC-TM-650 2.6.2.1 defined.
(6) it anti-flammability: is carried out according to 94 standard method of UL.
From the data comparison of table 1-5 it can be seen that
Comparative example 1 and embodiment 2 compare, and are situated between in comparative example 1 using copper-clad plate made by BHPPO and halogen-free epoxy resin
Electrical property is poor, heat resistance and humidity resistance are poor, Tg is low, and water absorption rate is high；Comparative example 2 and embodiment 6 compare, and make in comparative example 2
The copper-clad plate dielectric properties made by BHPPO and cyanate ester resin and halogen-free epoxy resin are poor, water absorption rate is high, heat resistance and
Humidity resistance difference and Tg are low；Comparative example 3 and embodiment 2 compare, and solidify halogen-free epoxy resin, phase using FRX3001 in comparative example 3
With under the conditions of, since FRX3001 reactivity is weak, OH-Content is low, and copper-clad plate can not be made；Comparative example 4 and embodiment 6 compare,
In comparative example 4 using copper-clad plate dielectric properties made by FRX3001 and the co-curing halogen-free epoxy resin of cyanate ester resin compared with
Difference, Tg is low, humidity resistance is poor, poor fire；Comparative example 5 and embodiment 14 compare, total with FRX-3001 and SMA in comparative example 5
Same cured epoxy resin, under the same terms, since FRX3001 reactivity is weak, OH-Content is low, and copper-clad plate can not be made.
In addition, comparative example 6 and embodiment 1 are compared it is found that being higher than in embodiment 1 in comparative example 6 using content
Acid anhydrides sealing end double hydroxyl fragrance oxygroup alkyl phosphine oxides when, made by copper-clad plate heat resistance and humidity resistance it is poor, Tg is low；It will
Comparative example 7 and embodiment 1 are compared double hydroxyls virtue it is found that in comparative example 7 using content lower than the acid anhydrides sealing end in embodiment 1
When fragrant oxygroup alkyl phosphine oxide, made by copper-clad plate humidity resistance is poor, poor fire.
It is by the above results as can be seen that fragrant by double hydroxyls that BHPPO and FRX are replaced with to acid anhydrides sealing end of the invention
Oxygroup alkyl phosphine oxide has up to 215 DEG C with prepreg and laminate for printed circuits made of halogen-free epoxy resin etc.
Glass transition temperature；Excellent dielectric properties, water absorption rate control in 0.06~0.1% range；High-fire resistance；Excellent
Humidity resistance and good technique processability；Excellent flame retarding efficiency, P content 1.98% can reach UL94 V-0.
In conclusion compared with general laminate, made of halogen-free thermosetting resin composite provided by the present invention
Prepreg and laminate for printed circuits have high glass-transition temperature, excellent dielectric properties, low water absorption, high heat resistance
Property, excellent humidity resistance and good technique processability, and it is able to achieve halogen-free flameproof, reach UL94 V-0 halogen-free flameproof.
The above, only presently preferred embodiments of the present invention for those of ordinary skill in the art can bases
Technical solution of the present invention and technical concept make other various corresponding changes and modifications, and all these change and modification are all
It should belong to the range of the claims in the present invention.
Claims (14)
1. a kind of compositions of thermosetting resin, which is characterized in that include epoxy resin and curing agent, wherein curing agent at least wraps
Containing a kind of phosphorous acid anhydrides, shown in structural formula such as formula (I)；
Wherein, R1ForAny one in naphthalene, the linear or branched alkyl group containing carbon number 1~4；
Wherein, n1For 0~5 integer；
Wherein, R3For any one in the linear or branched alkyl group containing carbon number 1~4；
Wherein, R2Any one in following group:
Wherein, any one of Ar in following group:
The phosphorous acid anhydrides accounts for 20%~60% of epoxy resin and curing agent total weight in the compositions of thermosetting resin；
The epoxy resin accounts for 30%~60% of epoxy resin and curing agent total weight in the compositions of thermosetting resin.
2. compositions of thermosetting resin as described in claim 1, which is characterized in that the phosphorous acid anhydrides accounts for the thermosetting property tree
The 20%~45% of epoxy resin and curing agent total weight in oil/fat composition.
3. compositions of thermosetting resin as claimed in claim 2, which is characterized in that the phosphorous acid anhydrides accounts for the thermosetting property tree
The 25%~40% of epoxy resin and curing agent total weight in oil/fat composition.
4. the compositions of thermosetting resin as described in one of claims 1 to 3, which is characterized in that the curing agent also includes cyanogen
Acid ester resin and/or bismaleimide-triazine resin.
5. compositions of thermosetting resin as claimed in claim 4, which is characterized in that the cyanate ester resin and/or span come
Acid imide-cyanate resin accounts for 2%~50% of epoxy resin and curing agent total weight in the compositions of thermosetting resin.
6. compositions of thermosetting resin as described in claim 1, which is characterized in that the curing agent also includes SMA resin.
7. compositions of thermosetting resin as claimed in claim 6, which is characterized in that the SMA resin accounts for the thermosetting property tree
The 2%~40% of epoxy resin and curing agent total weight in oil/fat composition.
8. compositions of thermosetting resin as described in claim 1, which is characterized in that the curing agent also includes phenolic resin.
9. compositions of thermosetting resin as claimed in claim 8, which is characterized in that the phenolic resin accounts for the thermosetting property tree
The 2%~20% of epoxy resin and curing agent total weight in oil/fat composition.
10. compositions of thermosetting resin as described in claim 1, which is characterized in that the compositions of thermosetting resin also wraps
Containing organic halogen-free flame retardants.
11. compositions of thermosetting resin as claimed in claim 10, which is characterized in that the organic halogen-free agent is phosphorous
Fire retardant.
12. compositions of thermosetting resin as claimed in claim 10, which is characterized in that in the compositions of thermosetting resin
Based on 100 parts by weight, the content of organic halogen-free agent is 1~15 parts by weight for epoxy resin and curing agent total amount.
13. compositions of thermosetting resin as described in claim 1, which is characterized in that the compositions of thermosetting resin also wraps
Containing filler and/or promotor.
14. compositions of thermosetting resin as described in one of claim 1~13 is in resin sheet, resin laminated metal foil, pre-
Soak the application in material, laminate, metal-clad laminate or printed wiring board.
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| CN201611080924.2A CN108117633B (en) | 2016-11-30 | 2016-11-30 | A kind of compositions of thermosetting resin |
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| CN201611080924.2A CN108117633B (en) | 2016-11-30 | 2016-11-30 | A kind of compositions of thermosetting resin |
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| CN108117633A CN108117633A (en) | 2018-06-05 |
| CN108117633B true CN108117633B (en) | 2019-08-27 |
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| CN114605779B (en) * | 2020-12-09 | 2023-09-12 | 广东生益科技股份有限公司 | Thermosetting resin composition, prepreg comprising thermosetting resin composition, circuit substrate and printed circuit board |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015054868A (en) * | 2013-09-10 | 2015-03-23 | Dic株式会社 | Phosphorus atom-containing active ester resin, epoxy resin composition, cured product thereof, prepreg, circuit board, and build-up film |
| WO2015096141A1 (en) * | 2013-12-27 | 2015-07-02 | 广东生益科技股份有限公司 | Thermosetting epoxy resin composition and use thereof |
| 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 |
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2016
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015054868A (en) * | 2013-09-10 | 2015-03-23 | Dic株式会社 | Phosphorus atom-containing active ester resin, epoxy resin composition, cured product thereof, prepreg, circuit board, and build-up film |
| WO2015096141A1 (en) * | 2013-12-27 | 2015-07-02 | 广东生益科技股份有限公司 | Thermosetting epoxy resin composition and use thereof |
| 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 |
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