CN108164684A - A kind of compositions of thermosetting resin - Google Patents
A kind of compositions of thermosetting resin Download PDFInfo
- Publication number
- CN108164684A CN108164684A CN201611114924.XA CN201611114924A CN108164684A CN 108164684 A CN108164684 A CN 108164684A CN 201611114924 A CN201611114924 A CN 201611114924A CN 108164684 A CN108164684 A CN 108164684A
- Authority
- CN
- China
- Prior art keywords
- resin
- compositions
- thermosetting resin
- epoxy resin
- curing agent
- 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.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 88
- 239000011347 resin Substances 0.000 title claims abstract description 88
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 42
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims abstract description 41
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 150000002148 esters Chemical class 0.000 claims abstract description 32
- 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 55
- 229920000647 polyepoxide Polymers 0.000 claims description 55
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229920001568 phenolic resin Polymers 0.000 claims description 14
- 239000005011 phenolic resin Substances 0.000 claims description 14
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 11
- 239000004643 cyanate ester Substances 0.000 claims description 11
- 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 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- LCDFWRDNEPDQBV-UHFFFAOYSA-N formaldehyde;phenol;urea Chemical compound O=C.NC(N)=O.OC1=CC=CC=C1 LCDFWRDNEPDQBV-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 238000010521 absorption reaction Methods 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 11
- 230000008901 benefit Effects 0.000 abstract description 3
- -1 DOPO class compounds Chemical class 0.000 description 25
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 24
- 239000003063 flame retardant Substances 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 14
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 14
- 239000011574 phosphorus Substances 0.000 description 14
- 229910052698 phosphorus Inorganic materials 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000805 composite resin Substances 0.000 description 10
- 239000004744 fabric Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000010792 warming Methods 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- KMRIWYPVRWEWRG-UHFFFAOYSA-N 2-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(P2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1 KMRIWYPVRWEWRG-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 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 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 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
- 239000012779 reinforcing material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 239000001110 calcium chloride Substances 0.000 description 5
- 229910001628 calcium chloride Inorganic materials 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 239000010949 copper Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000003963 dichloro group Chemical group Cl* 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 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
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 230000000979 retarding effect Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 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
- 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
- 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
- 230000009172 bursting Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000005213 imbibition Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 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
- 235000012239 silicon dioxide Nutrition 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
- LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-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
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-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
- 229960000549 4-dimethylaminophenol Drugs 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
- 0 C*(NCCC1NC1)I Chemical compound C*(NCCC1NC1)I 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 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 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
- 230000003750 conditioning effect Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002156 mixing Methods 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
- 150000003053 piperidines Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000010453 quartz Substances 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
- 238000007789 sealing Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 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
- 238000005406 washing Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical class CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-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
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- 150000004941 2-phenylimidazoles Chemical class 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- 150000003929 3-aminopyridines Chemical class 0.000 description 1
- ZDCFJCRHWNSQOL-UHFFFAOYSA-N 3-methylpiperidin-2-amine Chemical class CC1CCCNC1N ZDCFJCRHWNSQOL-UHFFFAOYSA-N 0.000 description 1
- OYRZFURJZQGZDP-UHFFFAOYSA-N 4,4-dimethylpiperidin-2-amine Chemical class NC1NCCC(C1)(C)C OYRZFURJZQGZDP-UHFFFAOYSA-N 0.000 description 1
- UHDGDGPBCVFSDJ-UHFFFAOYSA-N 4-methylpiperidin-2-amine Chemical class CC1CCNC(N)C1 UHDGDGPBCVFSDJ-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
- 241001120493 Arene Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical class OCC1CO1 CTKINSOISVBQLD-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
- CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 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
- 230000001154 acute effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 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
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 description 1
- LJUXFZKADKLISH-UHFFFAOYSA-N benzo[f]phosphinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=P1 LJUXFZKADKLISH-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000008859 change Effects 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
- 235000009508 confectionery Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 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
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 235000011187 glycerol 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
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 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
- 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 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
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- RMOCVWPGFARDJP-UHFFFAOYSA-N piperazine-2,6-diamine Chemical class NC1CNCC(N)N1 RMOCVWPGFARDJP-UHFFFAOYSA-N 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000002861 polymer material Substances 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
- 230000008569 process Effects 0.000 description 1
- 230000009257 reactivity Effects 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-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
- 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
- C08G59/4284—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with other curing agents
-
- 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
- C08G59/62—Alcohols or phenols
-
- 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
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- 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
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- 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
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- 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)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Reinforced Plastic Materials (AREA)
- Epoxy Resins (AREA)
Abstract
The present invention provides a kind of compositions of thermosetting resin, it includes ester terminated phosphorous polymers, the compositions of thermosetting resin has many advantages, such as good thermal stability, humidity resistance, toughness, dielectric constant and dielectric loss angle tangent is low, water absorption rate is low and high halogen-free flameproof efficiency, and with 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 technology
Traditional on July 1st, 2006, two parts of environmental protection instructions of European Union《It is instructed about electric/electronic device is scrapped》With《About
In the Restriction of the Use of Certain Hazardous Substances in Electrical and Electronic Equipment》It is formal to implement, the exploitation of halogen-free flameproof copper-clad laminate
As the hot spot of industry, each copper-clad laminate producer all releases the halogen-free flameproof copper-clad laminate of oneself one after another.
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.
Phosphorus flame retardant widely used on copper-clad plate field is broadly divided into two kinds of response type and addition type at present.Response type is mainly
DOPO class compounds, based on phosphorous epoxy resin, phosphorus containing phenolic resin, phosphorus content is between 2~10%.However, practical should
With middle discovery, DOPO classes compound has larger water absorption rate and poor dielectric properties and the plank humidity resistance poor.Addition type
Predominantly phosphonitrile and phosphonate ester compound, the flame retarding efficiency of additive flame retardant is relatively low, and needing to add more amount could reach
To flame-retardancy requirements.It is easy to migrate to plank in laminate process simultaneously because of its relatively low fusing point (generally below 150 DEG C)
Surface influences plate property.
In addition, for copper clad foil substrate material, in order to meet the performance of PCB processing performances 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 spy
Property, high peel strength, excellent humidity resistance.
DOPO-HQ is the phosphorus curing agent of reactivity, can be cured and react with epoxy resin, but due to its activity
Group is phenolic hydroxyl group, and the larger secondary hydroxyl of polarity can be generated after being reacted with epoxy resin, leads to the dielectric properties of solidfied material
It is poor.The preparation method and its purposes of the active ester with the connection alkyl containing phospho hetero phenanthrene are disclosed in CN103965249A, but containing phospha
Phenanthrene connection alkyl causes it slightly lower with Tg during epoxy resin cure, make its on High Tg CCL with being restricted.
It is disclosed in CN105669760A using phenanthrene derivative containing phospha and the inactive ester type compound of glycerine synthesis, it can be to add
The form added is fire-retardant to engineering material progress, and equally the Tg of reinforcing material is not contributed.It is mentioned in CN103694642A with poly-
Phosphonate ester or/and phosphonate ester-carbonic ester and epoxy resin, cyanate ester resin blending prepare copper-clad plate.Polyphosphonates in this system
Or/and phosphonate ester-carbonic ester has the heat resistance of system negative effect, and because of its phosphorus content as additive flame retardant
Relatively low, flame retarding efficiency is low.
Invention content
Through inventor the study found that can be formed using ester terminated phosphorous polymer as epoxy resin and its curing agent
Curing system addition fire retardant, but its higher fusing point and higher phosphorus content, relative to the phosphonic acids of common addition type
Ester fire retardant has unrivaled advantage.More than feature is based on, without adding or only needing to add other fire retardants on a small quantity
Plank is made to achieve the effect that UL94V-0 halogen-free flameproofs.
Based on this, one of the objects of the present invention is to provide a kind of compositions of thermosetting resin and its preimpregnation is used
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 can realize halogen-free flameproof, reach UL94V-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,
SMA resins and ester terminated phosphorous polymer and the composition that optionally other curing agent are suitably mixed to get, can reach
Above-mentioned purpose.
That is, the present invention adopts the following technical scheme that：A kind of compositions of thermosetting resin, it includes epoxy resin, curing agent
And ester terminated phosphorous polymer, wherein curing agent include at least SMA resins.
The compositions of thermosetting resin of the present invention is halogen-free thermosetting resin composite, with ester terminated phosphorous polymerization
Halogen-free flame retardants of the object as the curing system of epoxy resin.Its phosphorus content is high, fusing point is high, is added in epoxy curing systems,
Heat-resist, Tg high bittern-free flame-proof material can be obtained, need to only add on a small quantity or need not additionally add other fire retardants can
It is fire-retardant to reach UL94V-0.
The present invention is by the use of high content of phosphorus, dystectic ester terminated phosphorous polymer as the fire-retardant of epoxy curing systems
Agent can significantly improve the anti-flammability of the prepreg made using the resin combination and laminate for printed circuits, and
The glass transition temperature and heat resistance of plank will not be reduced, and makes it have good technique processability, and realize halogen-free flameproof, is reached
To UL94V-0.Each component is described in detail below.
According to the present invention, the ester terminated phosphorous polymer, shown in structural formula such as formula (I)：
Wherein, n1For 1~20 integer, for example, 1,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,
19 or 20；
Wherein, R1For any one in phenyl, naphthalene, xenyl, the linear or branched alkyl group containing carbon number 1~4；Wherein
Linear or branched alkyl group containing carbon number 1~4 for example can be methyl, ethyl, propyl, butyl, isopropyl, isobutyl group or tertiary butyl
In any one；
Wherein, Ar1For
In any one；
Wherein, Ar2ForIn any one；
Wherein, n2For 0~5 integer, such as 0,1,2,3,4 or 5；n3For 0~7 integer, such as 0,1,2,3,4,5,6
Or 7；
Wherein, R2For any one in the linear or branched alkyl group containing carbon number 1~4；The straight chain containing carbon number 1~4
Or branched alkyl for example can be any one in methyl, ethyl, propyl, butyl, isopropyl, isobutyl group or tertiary butyl.
Heretofore described ester terminated phosphorous polymer, structural formula can be such as lower structure：
Wherein, n1For 1~20 integer.
According to the present invention, the ester terminated phosphorous polymer account for the compositions of thermosetting resin epoxy resin,
The 10%~35% of curing agent and ester terminated phosphorous polymer total weight, for example, 10%, 12%, 14%, 15%,
16%th, the specific point value between 18%, 20%, 22%, 25%, 28%, 30%, 32% or 35% and above-mentioned numerical value, is limited to
Length and for it is concise the considerations of, the present invention specific point value that no longer range described in exclusive list includes.
According to the present invention, the epoxy resin accounts for the compositions of thermosetting resin epoxy resin, curing agent and ester
Base sealing end phosphorous polymer total weight 30%~55%, such as 30%, 32%, 34%, 35%, 36%, 38%, 40%,
42%th, the specific point value between 45%, 48%, 50%, 52% or 55% and above-mentioned numerical value, as space is limited and for simplicity
The considerations of, the present invention specific point value that no longer range described in exclusive list includes.
In the present invention, the epoxy resin is halogen-free epoxy resin, refer in 1 molecule tool there are two or two with
The epoxy resin of upper epoxy group, selected from glycidol ethers, glycidol esters, glycidol amine, alicyclic epoxy tree
In fat, epoxidation of olefins class, glycolylurea epoxide resin or acid imide epoxy resin any one or at least two mixture.
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.Above-mentioned epoxy resin is the epoxy resin of Halogen.
Preferably, the glycidol ethers are selected from the epoxy resin having the following structure：
Wherein, Z1、Z2And Z3It is each independently selected fromR3For hydrogen atom, substitution or
Any one in unsubstituted straight chained alkyl or branched alkyl containing carbon number 1~5.
Y1And Y2It is each independently selected from-CH2-、 In any one, n4It is 1~10
Arbitrary integer, such as 1,2,3,4,5,6,7,8,9 or 10, R4Straight chained alkyl or branch selected from hydrogen atom, containing carbon number 1~5
Any one in alkyl；Such as can be methyl, ethyl, propyl, butyl, amyl, isopropyl, isobutyl group, tertiary butyl or different
Any one in amyl.
Preferably, it is different to be selected from triglycidyl group-p- amino-phenols, triglycidyl group trimerization for the glycidol amine
Cyanate, four glycidyl group diamino dimethylene benzene, two amido diphenyl-methanes of four glycidyl group -4,4`-, four shrinks are sweet
Oil base -3,4`- diaminodiphenyl ethers, four glycidyl group -4,4`- diaminodiphenyl ethers or four glycidyl group -1,3- diaminos
In ylmethyl hexamethylene any one or at least two mixture.
The halogen-free thermosetting resin composite of the present 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 SMA resins may be used by styrene and maleic anhydride by 1:1~8:1 ratio copolymerization
It obtains, preferably has the following structure：
Wherein a is 1~8 integer, such as 1,2,3,4,5,6,7 or 8；B be 5~40 integer, such as 5,8,10,12,
15th, 18,25,28,30,35 or 40.
According to the present invention, the SMA resins account for the compositions of thermosetting resin epoxy resin, curing agent and ester group
The 35%~60% of the phosphorous polymer total weight of sealing end, for example, 35%, 37%, 38%, 40%, 42%, 45%, 48%,
50%th, the specific point value between 52%, 55%, 57%, 58% or 60% and above-mentioned numerical value, as space is limited and for simplicity
The considerations of, the present invention specific point value that no longer range described in exclusive list includes.
According to the present invention, the curing agent can also include cyanate ester resin and/or bismaleimide-triazine resin；
Wherein, the cyanate ester resin has the following structure：
Wherein, R13For-CH2-、
In any one or at least two mixture；R5、R6、R7、R8、R9、R10、R11Or R12It 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 tertiary butyl.
Preferably, the cyanate ester resin is selected from bis- (the 4- cyanato-s phenyl) propane of 2,2-, bis- (4- cyanato-s phenyl) second
Alkane, bis- (3,5- dimethyl -4- cyanato-s phenyl) methane, bis- (4- cyanato-s the phenyl) -1,1,1,3,3,3- hexafluoropropane of 2,2-,
α, α '-bis- (4- cyanato-s phenyl)-diisopropyl benzene, Cyclopeutadiene type cyanate, phenol novolak type cyanate, cresol novolac
Bis- (4- cyanato-s phenyl) the propane prepolymers of type cyanate, 2,2-, bis- (4- cyanato-s phenyl) ethane prepolymers, bis- (3,5- bis-
Methyl -4- cyanato-s phenyl) methane prepolymer, bis- (4- cyanato-s the phenyl) -1,1,1,3,3,3- hexafluoropropane prepolymers of 2,2-,
α, α '-bis- (4- cyanato-s phenyl)-diisopropyl benzene prepolymers, dicyclopentadiene type ethylene rhodanate prepolymer, phenol novolak type
In cyanate prepolymer or cresol novolak type cyanate prepolymer any one or at least two mixture, preferably 2,2-
Bis- (4- cyanato-s phenyl) propane, α, α '-bis- (4- cyanato-s phenyl)-diisopropyl benzene, bis- (3,5- dimethyl -4- cyanogen oxygen
Base phenyl) methane, bis- (4- cyanato-s phenyl) the propane prepolymers of 2,2-, α, α '-bis- (4- cyanato-s phenyl)-diisopropyl benzene
In prepolymer or bis- (3,5- dimethyl -4- cyanato-s 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 the 0%~20% of object epoxy resin and curing agent total weight, for example, 0%, 2%, 4%, 5%, 8%, 10%, 12%,
14%th, the specific point value between 15%, 17% or 20% and above-mentioned numerical value, as space is limited and for it is concise the considerations of, this hair
The specific point value that range described in bright 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, the phenolic resin being known in the art, the present invention do not do particular determination.
According to the present invention, the phenolic resin accounts for the compositions of thermosetting resin epoxy resin and curing agent total weight
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 it is concise the considerations of, present invention tool that no longer range described in exclusive list includes
Body point value.
Heretofore described compositions of thermosetting resin, organic solid content specifically include based on 100 parts by weight：Halogen
Epoxy resin：30~55 parts by weight；35~60 parts by weight of SMA resins；Ester terminated phosphorous polymer：10~35 parts by weight；
Cyanate ester resin and/or bismaleimide-triazine resin：0~20 parts by weight；Phenolic resin：0~20 parts by weight.
" the compositions of thermosetting resin epoxy resin, curing agent and ester terminated mentioned in the present invention
In phosphorous polymer total weight ", curing agent refers to play the role of the SMA resins and optionally cyanate resin of cured epoxy resin
Fat and/or bismaleimide-triazine resin and phenolic resin.
The compositions of thermosetting resin of the present invention can also include phosphonium flame retardant.
According to the present invention, the phosphonium flame retardant can be selected from three (2,6- 3,5-dimethylphenyl) phosphines, 10- (2,5- dihydroxy
Phenyl) miscellaneous -10- phosphines phenanthrene -10- oxides of -9,10- dihydro-9-oxies, 2,6- bis- (2,6- 3,5-dimethylphenyls) phosphino- benzene, 10- benzene
Miscellaneous -10- phosphines phenanthrene -10- the oxides of base -9,10- dihydro-9-oxies, phenoxy phosphazene compound, phosphate, polyphosphate, polyphosphonic acid
In ester or phosphonate ester-carbonate copolymer any one or at least two mixture.
The halogen-free thermosetting resin composite of the present invention can also further 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- phenylimidazoles or 2-
In undecyl imidazole any one or at least two mixture.
Preferably, the piperidines are 2,3- diaminos phenylpiperidines, 2,5- diaminos phenylpiperidines, 2,6- diamino piperazines
Pyridine, 2- amino -3- methyl piperidines, 2- amino -4- methyl piperidines, 2- amino -3- nitros piperidines, 2- amino -5- nitros piperidines or
In 2- amino -4,4- lupetidines any one or at least two mixture.
Preferably, the pyridine compounds and their is 4-dimethylaminopyridine, 2-aminopyridine, 3- aminopyridines or 4- amino
Any one in pyridine or at least two mixtures.
Preferably, with ester terminated phosphorous polymer, epoxy resin and SMA resins and the cyanate resin that may be added
Fat, phenolic resin the sum of additive amount be 100 parts by weight meters, the additive amount of the curing accelerator is 0.01~1 parts by weight, example
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 weight
Part, 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.
The halogen-free thermosetting resin composite of the present invention can also further 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 conditioning agent of the surface treatment
Join agent in any one or at least two mixture.
Preferably, it is counted by 100 parts by weight of inorganic filler, the dosage of the surface conditioning 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,
Powdered quartz, 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, with ester terminated phosphorous polymer, epoxy resin and SMA resins and the cyanate resin that may be added
Fat, phenolic resin the sum of additive amount be 100 parts by weight meters, the additive amount of the filler is 5~300 parts by weight, preferably 5~
200 parts by weight, further preferred 5~150 parts by weight.
"comprising" of the present invention, it is intended that it can also include other components, these other components in addition to the component
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, ultra-violet absorber, pigment, colorant or lubricant etc..These additives can be single
It solely uses, two kinds or two or more can also be used in mixed way.
The preparation method of the halogen-free thermosetting resin composite of the present invention is ordinary skill in the art means, specific side
Method is：First solid content is put into, then adds in liquid solvent, is stirred to solid content after being completely dissolved, add liquid resin and
Accelerating agent 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
Wait 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.More than solvent can be used alone, also can 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.
The prepreg of the present invention is attached to the nothing as described above on reinforcing material including reinforcing material and impregnation after dry
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 select aramid nonwoven, the inorfil woven cloth can be E- glass-fiber-fabrics,
D- glass-fiber-fabrics, S- glass-fiber-fabrics, T glass-fiber-fabrics, NE- glass-fiber-fabrics 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.
The laminate for printed circuits of the present invention is included by being heated and pressurizeed, gluing prepreg more than a piece of or two panels
Be combined and manufactured laminate and the metal foil that is bonded in more than laminate one or both sides.The laminate is
Cure 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 foils etc., material is unlimited.
Compared with prior art, the present invention at least has the advantages that：
The present invention is by the use of high content of phosphorus, dystectic ester terminated phosphorous polymer as the fire-retardant of epoxy curing systems
Agent can significantly improve the flame retarding efficiency of the prepreg made using the resin combination and laminate for printed circuits, and
And the glass transition temperature and heat resistance of plank will not be reduced, using made of halogen-free thermosetting resin composite provided by the invention
Prepreg and laminate for printed circuits have up to 245 DEG C of glass transition temperature；Excellent dielectric properties, water absorption rate
Control is in the range of 0.06-0.09%；High-fire resistance；Excellent humidity resistance and good technique processability；Excellent is fire-retardant
Efficiency can reach UL94V-0.
Specific embodiment
The technical solution further illustrated the present invention below by specific embodiment.
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, under the premise of principle of the embodiment of the present invention is not departed from, several improvements and modifications can also be made, these improvement
The protection domain of the embodiment of the present invention is also considered as 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, can suitably change implementation.
1st, the synthesis of phosphorous polymer P-AE1
By 320g ODOPB and 185g diphenylphosphoryl dichloros and 1.11g calcium chloride add in equipped with blender, condensing reflux pipe,
It is stirred in the four-necked bottle of thermometer, while is passed through nitrogen, be then warming up to 160 DEG C, react 1.5h at this temperature.It then will be anti-
Temperature rise is answered to 230 DEG C, and reacts 5h at this temperature.Then room temperature is reduced the temperature to, and adds in dichloromethane dissolving tree
Fat, then 13.7g chlorobenzoyl chlorides are added in reaction system, 1.5h is reacted at this temperature.Then 5% sodium carbonate liquor is added in, and
It is vigorously stirred, filters, washes, dries, obtain product, number P-AE1.
Wherein n1=20
2nd, the synthesis of phosphorous polymer P-AE2
By 370g 10- (2,5- dihydroxy naphthalene) -10- hydrogen -9- oxa- -10- phospho hetero phenanthrene -10- oxides, 175g phenyl
Phosphinylidyne dichloro and 1.11g calcium chloride in equipped with blender, condensing reflux pipe, thermometer four-necked bottle in stir, while be passed through nitrogen
Then gas is warming up to 160 DEG C, reacts 1.5h at this temperature.Then 230 DEG C are warming up to, and 5h is reacted under logical condition of nitrogen gas.
It is then cooled to room temperature, and adding in dichloromethane dissolves resin, then 2,4,6- trimethylbenzenes of 36.6g is added in reaction system
Phenol equally reacts 2h at this temperature.Then 5% sodium carbonate liquor is added in, and is vigorously stirred, filters, wash, dry, obtain
Product, number P-AE2.
Wherein n1=10
3rd, the synthesis of phosphorous polymer P-AE3
By 370g 10- (2,5- dihydroxy naphthalene) -10- hydrogen -9- oxa- -10- phospho hetero phenanthrene -10- oxides, 195.6g naphthalenes
Base phosphinylidyne dichloro and 1.11g calcium chloride in equipped with blender, condensing reflux pipe, thermometer four-necked bottle in stir, be passed through simultaneously
Then nitrogen is warming up to 160 DEG C, reacts 2h at this temperature.Under logical condition of nitrogen gas, 230 DEG C are warming up to, and at this temperature
React 5h.It is then cooled to room temperature, and adds in dichloromethane and dissolve resin.78.7g is added in tertiary butyl to reaction system again
Chlorobenzoyl chloride equally reacts 2h at this temperature.Then 5% sodium carbonate liquor is added in, and is vigorously stirred, filters, wash, do
It is dry, obtain product, number P-AE3.
Wherein n1=5
4th, the synthesis of phosphorous polymer P-AE4
By 320g ODOPB, 93.1g methyl phosphinylidyne dichloros and 1.11g calcium chloride in equipped with blender, condensing reflux pipe, temperature
It spends in the four-necked bottle of meter and stirs, while be passed through nitrogen, be then warming up to 160 DEG C, react 1h at this temperature.In logical condition of nitrogen gas
Under, 230 DEG C are warming up to, and react 5h at this temperature.It is then cooled to room temperature, adds in dichloromethane, dissolve resin, then to
Reaction system adds in 92.76g to methyl benzoyl chloride, reacts 1h at this temperature.Then 5% sodium carbonate liquor is added in, and acute
Strong stirring, filtering, washing, drying, obtains product, number P-AE4.
Wherein n1=3
5th, the synthesis of phosphorous polymer P-AE5
By 370g 10- (2,5- dihydroxy naphthalene) -10- hydrogen -9- oxa- -10- phospho hetero phenanthrene -10- oxides, 79.8g methyl
Phosphinylidyne dichloro and 1.11g calcium chloride in equipped with blender, condensing reflux pipe, thermometer four-necked bottle in stir, while be passed through nitrogen
Then gas is warming up to 160 DEG C, reacts 1h at this temperature.Under logical condition of nitrogen gas, 230 DEG C are warming up to, and anti-at this temperature
Answer 5h.It is then cooled to room temperature, and adds in dichloromethane and dissolve resin, then 152.5g 2- naphthalene formyls are added in reaction system
Chlorine equally reacts 1h at this temperature.Product is cooled to room temperature and then adds in 5% sodium carbonate liquor, and be vigorously stirred, mistake
Filter, washing, drying, obtain product, number P-AE5.
Wherein n1=1
By ester terminated phosphorous polymer P-AE, halogen-free epoxy resin, curing agent and curing accelerator, halogen-free flameproof
Agent, filler are uniformly mixed in solvent by a certain percentage, and control glue solid content is 65%, impregnate above-mentioned glue with 2116 glass-fiber-fabrics
Liquid controls suitable thickness, and 2~15min is then toasted in 115~175 DEG C of baking oven is made prepreg, then by several preimpregnation
Material stacks, and is 170~250 DEG C in solidification temperature, solidifying pressure is 25~60kg/ in the stacked on 18 μ RTF copper foils in its both sides
cm2, is copper-clad plate is made under the conditions of 60~300min in hardening time.
Embodiment 1~14 and comparative example 1~8 are related to material and trade mark information is as follows：
(A) phosphorous polymer P-AE fire retardants are made by oneself
P-AE1：Make phosphorous polymer P-AE1 fire retardants by oneself
Wherein n1=20.
P-AE2：Make phosphorous polymer P-AE2 fire retardants by oneself
Wherein n1=10.
P-AE3：Make phosphorous polymer P-AE3 fire retardants by oneself
Wherein n1=5.
P-AE4：Make phosphorous polymer P-AE4 fire retardants by oneself
Wherein n1=3.
P-AE5：Make phosphorous polymer P-AE5 fire retardants by oneself
Wherein n1=1.
ODOPB：10- (2,5- dihydroxy phenyls) -10- hydrogen -9- oxa- -10- phospho hetero phenanthrene -10- oxides
FRX-3001：
(B) 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
(C) SMA resins
EF1000：SMA, styrene-maleic anhydride copolymer, Sartomer
EF40：SMA, styrene-maleic anhydride copolymer, Sartomer
EF60：SMA, styrene-maleic anhydride copolymer, Sartomer
EF80：SMA, styrene-maleic anhydride copolymer, Sartomer
(D) cyanate
CY-40：Wuqiao resin factory, DCPD type cyanate ester resins
PT60S：LONCZ, Novolac Cyanate Ester Resins
CE01PS：Jiangsu apocalypse, bisphenol A cyanate ester resin
CE01MO：Jiangsu apocalypse, bisphenol A cyanate ester resin
(E) 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)
(F) phosphonium flame retardant
SPB-100：Great mound chemistry, phosphine nitrile fire retardant, phosphorus content 13.4%
(G) accelerating agent
2E4MZ：2-ethyl-4-methylimidazole, four countries' chemical conversion
DMAP：4-dimethylaminopyridine, wide Rong Huaxue
BICAT Z：Zinc Isoocatanoate, The Shepherd Chemical Company
(H) filler
Fused silica (average grain diameter is 0.2 to 10 μm, more than 99% purity)
Table 1-3 is embodiment 1~14, the formula composition and its physical data of 4 comparative example 1~8 of table.
Table 1
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | |
| P-AE1 | 10 | ||||
| P-AE2 | 20 | ||||
| P-AE3 | 35 | ||||
| P-AE4 | 10 | 10 | |||
| P-AE5 | 10 | ||||
| EF1000 | 35 | 35 | |||
| EF40 | 40 | ||||
| EF60 | 50 | ||||
| EF80 | 60 | ||||
| HP-9900 | 55 | ||||
| NC-3000H | 30 | 40 | 30 | ||
| SKE-1 | 30 | ||||
| SPB-100 | 10 | 10 | |||
| 2E4MZ | |||||
| DMAP | 0.01 | 0.05 | 0.1 | 0.2 | 0.5 |
| Ball silicon | 0 | 25 | 25 | 25 | 300 |
| P% | 3.49% | 2.31% | 2.10% | 2.37% | 2.44% |
| Tg(DMA)/℃ | 185 | 190 | 185 | 190 | 185 |
| Dk(10GHz) | 4 | 4 | 3.9 | 3.8 | 4.2 |
| Df(10GHz) | 0.008 | 0.0075 | 0.0075 | 0.0075 | 0.0071 |
| Water imbibition/% | 0.08 | 0.07 | 0.07 | 0.07 | 0.05 |
| PCT/6h | OOO | OOO | OOO | OOO | OOO |
| T288/min | ＞ 60 | ＞ 60 | ＞ 60 | ＞ 60 | ＞ 60 |
| Difficult to burn | V-0 | V-0 | V-0 | V-0 | V-0 |
Table 2
Table 3
Table 4
PCT/6h performance maps target remarks additionally：× to be layered plate bursting, O is not stratified plate bursting.
The test method of more than characteristic is as follows：
(1) glass transition temperature (Tg)：It is tested using DMA, is surveyed according to the DMA of IPC-TM-650 2.4.24 defineds
Method for testing is measured.
(2) dielectric constant and dielectric loss factor：It is tested according to SPDR methods.
(3) humidity resistance (PCT) is evaluated：After the copper foil on copper-clad plate surface is etched, substrate is evaluated；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 stove, 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 stove more than 5min.
(4)T288：With TMA instrument, it is measured according to the T300 test methods of IPC-TM-650 2.4.24.1 defineds.
(5) water imbibition：Water imbibition test method according to IPC-TM-650 2.6.2.1 defineds is measured.
(6) anti-flammability：It is carried out according to 94 standard methods of UL.
The following is can be seen that from the data comparison of table 1-4：
Comparative example 1 and embodiment 3 compare, using made by ODOPB, SMA resin and halogen-free epoxy resin in comparative example 1
Copper-clad plate dielectric properties are poor, heat resistance and humidity resistance are poor, water absorption rate is high and poor fire；Comparative example 2 and embodiment 7
Compare, in comparative example 2 using the copper-clad plate Tg made by ODOPB, SMA resin and cyanate ester resin and halogen-free epoxy resin it is low,
Water absorption rate is high, heat resistance and humidity resistance are poor, and poor fire；Comparative example 3 and embodiment 12 compare, and make in comparative example 3
With copper-clad plate water absorption rate height, heat resistance and the wet-heat resisting made by ODOPB, SMA resin and phenolic resin and halogen-free epoxy resin
Property is poor；Comparative example 4 and embodiment 3 compare, using made by FRX3001 and SMA resins and halogen-free epoxy resin in comparative example 4
Copper-clad plate dielectric properties are poor, water absorption rate is high, heat resistance and humidity resistance are poor, and Tg is low, and poor fire；Comparative example 5 and reality
It applies example 7 to compare, covers copper using made by FRX3001, SMA resin and cyanate ester resin and halogen-free epoxy resin in comparative example 5
Plate Tg is low, water absorption rate is high, heat resistance and humidity resistance are poor, and poor fire；Comparative example 6 and embodiment 12 compare, comparison
FRX3001, SMA resin and copper-clad plate water absorption rate made by phenolic resin and halogen-free epoxy resin is high, heat resistance and resistance in example 6
Humid is poor.
In addition, comparative example 7 and embodiment 5 are compared it is found that using content less than in embodiment 5 in comparative example 7
During ester terminated phosphorous polymer, made by copper-clad plate dielectric properties it is poor；Comparative example 8 and embodiment 1 are compared
Compared with it is found that in comparative example 8 using content higher than ester terminated phosphorous polymer in embodiment 1 when, made by cover copper
Plate Tg is low, heat resistance and humidity resistance are poor.
By the above results as can be seen that by the way that ODOPB and FRX to be replaced with to ester terminated phosphorous polymerization of the invention
Object, with SMA resins and halogen-free epoxy resin etc. made of prepreg and laminate for printed circuits, there are up to 245 DEG C
Glass transition temperature；Excellent dielectric properties, water absorption rate are controlled in the range of 0.06-0.09%；High-fire resistance；Excellent is resistance to
Humid and good technique processability；Excellent flame retarding efficiency can reach UL94 V-0.
As described above, compared with general laminate, made of halogen-free thermosetting resin composite provided by the present invention
Prepreg and laminate for printed circuits are heat-resisting with high glass-transition temperature, excellent dielectric properties, low water absorption, height
Property, excellent humidity resistance and good technique processability, and can realize halogen-free flameproof, reach UL94 V-0.
The above, only presently preferred embodiments of the present invention, for those of ordinary skill in the art, can basis
Technical scheme of the present invention and technical concept make other various corresponding changes and deformation, and all these changes and deformation are all
The range of the claims in the present invention should be belonged to.
Claims (8)
1. a kind of compositions of thermosetting resin, which is characterized in that include epoxy resin, curing agent and ester terminated phosphorous poly-
Close object；
The curing agent includes at least SMA resins；
Shown in the ester terminated phosphorous polymer structural formula such as formula (I)；
Wherein, n1For 1~20 integer；
Wherein, R1For any one in phenyl, naphthalene, xenyl, the linear or branched alkyl group containing carbon number 1~4；
Wherein, Ar1For
In any one；
Wherein, Ar2ForIn any one；
Wherein, n2For 0~5 integer；n3For 0~7 integer；
Wherein, R2For any one in the linear or branched alkyl group containing carbon number 1~4；
The epoxy resin accounts for the compositions of thermosetting resin epoxy resin, curing agent and ester terminated phosphorous polymerization
The 30%~55% of object total weight；
The SMA resins account for the compositions of thermosetting resin epoxy resin, curing agent and ester terminated phosphorous polymerization
The 35%~60% of object total weight；
The ester terminated phosphorous polymer accounts for the compositions of thermosetting resin epoxy resin, curing agent and ester group envelope
The 10%~35% of the phosphorous polymer total weight at end.
2. compositions of thermosetting resin as described in claim 1, which is characterized in that the SMA resins are styrene and Malaysia
Acid anhydrides presses 1:1~8:1 ratio is copolymerized to obtain.
3. compositions of thermosetting resin as claimed in claim 1 or 2, which is characterized in that the curing agent also includes cyanate
Resin and/or bismaleimide-triazine resin.
4. compositions of thermosetting resin as claimed in claim 3, which is characterized in that the cyanate ester resin and/or span come
Acid imide-cyanate resin accounts for the 0%~20% of the compositions of thermosetting resin epoxy resin and curing agent total weight.
5. the compositions of thermosetting resin as described in one of Claims 1 to 4, which is characterized in that the curing agent also includes phenol
Urea formaldehyde.
6. compositions of thermosetting resin as claimed in claim 5, which is characterized in that the phenolic resin accounts for the thermosetting property tree
The 0%~20% of oil/fat composition epoxy resin and curing agent total weight.
7. the compositions of thermosetting resin as described in one of claim 1~6, which is characterized in that the thermosetting resin combination
Object also includes filler and/or accelerating agent.
8. the compositions of thermosetting resin as described in one of claim 1~7 is in resin sheet, resin laminated metal foil, preimpregnation
Application in material, laminate, metal-clad laminate or printed wiring board.
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