CN111534076A - Polyarylether base composition containing reversible thermal shrinkage and cold expansion structural unit and prepreg and thermosetting copper-clad plate prepared from polyarylether base composition - Google Patents
Polyarylether base composition containing reversible thermal shrinkage and cold expansion structural unit and prepreg and thermosetting copper-clad plate prepared from polyarylether base composition Download PDFInfo
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- CN111534076A CN111534076A CN202010447844.6A CN202010447844A CN111534076A CN 111534076 A CN111534076 A CN 111534076A CN 202010447844 A CN202010447844 A CN 202010447844A CN 111534076 A CN111534076 A CN 111534076A
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- Prior art keywords
- polyarylether
- thermal shrinkage
- resin
- composition containing
- reversible thermal
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 229920000090 poly(aryl ether) Polymers 0.000 title claims abstract description 51
- 230000002441 reversible effect Effects 0.000 title claims abstract description 34
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 13
- 229920005989 resin Polymers 0.000 claims abstract description 47
- 239000011347 resin Substances 0.000 claims abstract description 47
- 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 claims abstract description 20
- 239000003063 flame retardant Substances 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 239000011159 matrix material Substances 0.000 claims abstract description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000945 filler Substances 0.000 claims abstract description 10
- 239000011889 copper foil Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000003822 epoxy resin Substances 0.000 claims description 17
- 229920000647 polyepoxide Polymers 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- -1 monoamine Chemical class 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000012295 chemical reaction liquid Substances 0.000 claims description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 7
- 238000010030 laminating Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000003365 glass fiber Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 4
- 229920000271 Kevlar® Polymers 0.000 claims description 4
- 239000004642 Polyimide Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910003080 TiO4 Inorganic materials 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000011324 bead Substances 0.000 claims description 4
- WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(iii) oxide Chemical compound O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 4
- 239000004917 carbon fiber Substances 0.000 claims description 4
- 239000004643 cyanate ester Substances 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 239000004761 kevlar Substances 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001844 chromium Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- 229910002929 BaSnO3 Inorganic materials 0.000 claims description 2
- 229920002748 Basalt fiber Polymers 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910004774 CaSnO3 Inorganic materials 0.000 claims description 2
- 229910002971 CaTiO3 Inorganic materials 0.000 claims description 2
- 229910002976 CaZrO3 Inorganic materials 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 229910003781 PbTiO3 Inorganic materials 0.000 claims description 2
- 229910020698 PbZrO3 Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 2
- 239000004697 Polyetherimide Substances 0.000 claims description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 2
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
- 229910004410 SrSnO3 Inorganic materials 0.000 claims description 2
- 229910002370 SrTiO3 Inorganic materials 0.000 claims description 2
- 229910010252 TiO3 Inorganic materials 0.000 claims description 2
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 claims description 2
- 229910007694 ZnSnO3 Inorganic materials 0.000 claims description 2
- 229910003122 ZnTiO3 Inorganic materials 0.000 claims description 2
- JCLOGSKIMBJQAA-UHFFFAOYSA-N [Mo].[Sn] Chemical compound [Mo].[Sn] JCLOGSKIMBJQAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910002113 barium titanate Inorganic materials 0.000 claims description 2
- 229910021523 barium zirconate Inorganic materials 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 2
- YGBGWFLNLDFCQL-UHFFFAOYSA-N boron zinc Chemical compound [B].[Zn] YGBGWFLNLDFCQL-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 150000004662 dithiols Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 229910001679 gibbsite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 150000002696 manganese Chemical class 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229920002530 polyetherether ketone Polymers 0.000 claims description 2
- 229920001601 polyetherimide Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 238000005245 sintering Methods 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- 229910014031 strontium zirconium oxide Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 239000002344 surface layer Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 238000003475 lamination Methods 0.000 claims 3
- 229920013636 polyphenyl ether polymer Polymers 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 2
- 238000004026 adhesive bonding Methods 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 238000004891 communication Methods 0.000 abstract description 2
- 239000003292 glue Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- YXZPTVOCJLCMRO-UHFFFAOYSA-N 2-bromo-6-methylphenol Chemical compound CC1=CC=CC(Br)=C1O YXZPTVOCJLCMRO-UHFFFAOYSA-N 0.000 description 2
- CIRRFAQIWQFQSS-UHFFFAOYSA-N 6-ethyl-o-cresol Chemical compound CCC1=CC=CC(C)=C1O CIRRFAQIWQFQSS-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- ATGFTMUSEPZNJD-UHFFFAOYSA-N 2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 ATGFTMUSEPZNJD-UHFFFAOYSA-N 0.000 description 1
- NAILKKRDWBJCNH-UHFFFAOYSA-N 2,6-dipropylphenol Chemical compound CCCC1=CC=CC(CCC)=C1O NAILKKRDWBJCNH-UHFFFAOYSA-N 0.000 description 1
- MTUHNOQQFRNDBN-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)phenol Chemical compound CC1=CC=CC(C)=C1C1=CC=CC=C1O MTUHNOQQFRNDBN-UHFFFAOYSA-N 0.000 description 1
- KTIRRDOBTNZKNL-UHFFFAOYSA-N 2-bromo-6-ethylphenol Chemical compound CCC1=CC=CC(Br)=C1O KTIRRDOBTNZKNL-UHFFFAOYSA-N 0.000 description 1
- XNJCFOQHSHYSLG-UHFFFAOYSA-N 2-chloro-6-ethylphenol Chemical compound CCC1=CC=CC(Cl)=C1O XNJCFOQHSHYSLG-UHFFFAOYSA-N 0.000 description 1
- TVOICAOPKRBXDY-UHFFFAOYSA-N 2-methyl-6-(2-methylphenyl)phenol Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)C)=C1O TVOICAOPKRBXDY-UHFFFAOYSA-N 0.000 description 1
- NXSQQKKFGJHACS-UHFFFAOYSA-N 2-methyl-6-propylphenol Chemical compound CCCC1=CC=CC(C)=C1O NXSQQKKFGJHACS-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- XHFVDZNDZCNTLT-UHFFFAOYSA-H chromium(3+);tricarbonate Chemical compound [Cr+3].[Cr+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O XHFVDZNDZCNTLT-UHFFFAOYSA-H 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- WIVXEZIMDUGYRW-UHFFFAOYSA-L copper(i) sulfate Chemical compound [Cu+].[Cu+].[O-]S([O-])(=O)=O WIVXEZIMDUGYRW-UHFFFAOYSA-L 0.000 description 1
- LZJJVTQGPPWQFS-UHFFFAOYSA-L copper;propanoate Chemical compound [Cu+2].CCC([O-])=O.CCC([O-])=O LZJJVTQGPPWQFS-UHFFFAOYSA-L 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ZYZHMSJNPCYUTB-UHFFFAOYSA-N n-benzyl-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(C)NCC1=CC=CC=C1 ZYZHMSJNPCYUTB-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass fibres
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J2427/18—Homopolymers or copolymers of tetrafluoroethylene
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Abstract
The invention belongs to the field of communication materials, and particularly relates to a polyarylether-based composition containing reversible thermal shrinkage and cold expansion structural units, and a prepreg and a thermosetting copper-clad plate prepared from the polyarylether-based composition. The preparation method comprises the steps of firstly preparing the double-end hydroxyl type polyphenyl ether resin containing the dibenzo eight-membered ring structural unit, taking the double-end hydroxyl type polyphenyl ether resin as a matrix resin, then assisting with a proper main curing agent, a proper secondary curing agent, a curing accelerator, a filler and a flame retardant, and preparing the prepreg containing the dibenzo eight-membered ring structural unit by processes of gluing, baking and the like. The prepreg has the advantages of uniform glue content, strong resin adhesive force, smooth surface, and proper toughness and viscosity, and the thermosetting copper-clad plate prepared from the prepreg has excellent dielectric property, high mechanical strength, high copper foil peeling strength and good uniformity of various properties. Particularly, the thermal expansion coefficient of the copper-clad plate can be controllably reduced by adjusting the molecular weight of the double-end hydroxyl type polyphenyl ether resin containing the dibenzo eight-membered ring structural unit and the content of the double-end hydroxyl type polyphenyl ether resin in the prepreg.
Description
Technical Field
The invention belongs to the field of communication materials, and particularly relates to a polyarylether-based composition containing reversible thermal shrinkage and cold expansion structural units, and a prepreg and a thermosetting copper-clad plate prepared from the polyarylether-based composition.
Background
Electronic products are rapidly developing towards miniaturization, light weight, thinning and multi-functionalization, and copper-clad plates serving as main carriers of electronic components have higher and higher integration level and more obvious multi-layering trend, so that the copper-clad plates are required to have extremely low thermal expansion coefficients. The traditional idea is to introduce a large amount of inorganic filler into a plate matrix to inhibit the thermal expansion process of a polymer matrix, however, a significant limit value exists for the reduction effect of the thermal expansion coefficient of the copper-clad plate brought by the scheme. In addition, the introduction of excessive inorganic filler can cause problems such as poor dispersibility of materials in the matrix of the sheet material, poor uniformity and reliability of the sheet material properties, and the like.
In 2013, the Jennifer Lu subject group of the university of California and the Wang Changchun subject group of the university of Redand jointly discover that the polymer containing the dibenzo eight-membered ring structural unit has unique reversible thermal shrinkage and cold expansion characteristics, and the coefficient of thermal expansion of the polymer can be more than 1200ppm/K (nat. chem., 2013, 5, 1035; Chinese patent application 201710360230.2; Chinese patent application 201910474075.6), and the characteristic is derived from reversible conformation change of the dibenzo eight-membered ring structural unit from a twist ship type to a chair type.
The polyphenyl ether and the polyolefin resin have excellent dielectric property, so that the copper-clad plate can be manufactured. Nowadays, a thermosetting copper clad laminate modified by polyphenylene oxide and polydiene has been developed.
Disclosure of Invention
The invention aims to provide a polyarylether base composition containing reversible thermal shrinkage and cold expansion structural units, and a prepreg and a thermosetting copper-clad plate prepared from the polyarylether base composition.
The double-end hydroxyl type polyphenyl ether resin containing the dibenzo eight-membered ring structural unit is prepared by taking the double-end hydroxyl type polyphenyl ether resin as a matrix resin, and then assisting with a proper main curing agent, a proper secondary curing agent, a curing accelerator, a filler and a flame retardant, and the prepreg containing the dibenzo eight-membered ring structural unit is prepared by processes of gluing, baking and the like. The prepreg has the advantages of uniform gel content, strong resin adhesive force, smooth surface, and proper toughness and viscosity. Furthermore, the thermosetting copper-clad plate prepared from the prepreg has excellent dielectric property, high mechanical strength, high copper foil peeling strength and good uniformity of various properties. In particular, the thermal expansion coefficient of the copper-clad plate can be controllably reduced by adjusting the molecular weight of the double-end hydroxyl type polyphenyl ether resin containing dibenzo eight-membered ring structural units and the content of the double-end hydroxyl type polyphenyl ether resin in prepregs.
The invention provides a polyarylether base composition containing reversible thermal shrinkage and cold expansion structural units, which comprises more than seven components of matrix resin, modified resin, a main curing agent, a secondary curing agent, a curing accelerator, a filler and a flame retardant; the base resin is double-end hydroxyl type polyarylether resin containing a structural unit with reversible thermal shrinkage and cold expansion characteristics, and the specific structure is as follows:
d \ Program Files (x86) \ gwssi \ CPC client \ cases \ inventions \ dbfdb876-bf66-453b-a1a8-5b5693e6051e \ new \100002\ dest _ path _ image002 |
Wherein R1, R2, R3 and R4 each independently represent H, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group and a halogen atom; a is more than or equal to 0; r is specifically one or a composite of two of the following structures:
the matrix resin accounts for 4-25 wt% of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit.
The further preferred technical scheme is as follows: the specific preparation method of the double-end hydroxyl type polyarylether resin containing the dibenzo eight-membered ring structural unit comprises the following steps:
step 1, adding a catalyst into a solution of a phenol derivative monomer, and uniformly stirring to obtain a reaction solution A; preparing a solution of a monomer I or a monomer II, and marking as a reaction solution B; setting the reaction temperature to be 20-60 ℃, slowly dropwise adding the reaction liquid A into the reaction liquid B under the condition of introducing oxygen-containing gas while stirring, and continuously reacting for 4-72 hours after dropwise adding to obtain a product solution;
d \ Program Files (x86) \ gwssi \ CPC client \ cases \ inventions \ dbfdb876-bf66-453b-a1a8-5b5693e6051e \ new \100002\ dest _ path _ image006.jpg |
D \ Program Files (x86) \ gwssi \ CPC client \ cases \ inventions \ dbfdb876-bf66-453b-a1a8-5b5693e6051e \ new \100002\ dest _ path _ image008.jpg |
| Monomer I | Monomer II |
And 2, adding a poor solvent of the polyarylether resin into the product solution, uniformly stirring, standing until the polyarylether resin product is fully separated out and settled, and filtering, washing and drying to obtain the double-end hydroxyl type polyarylether resin containing the dibenzo eight-membered ring.
The further preferred technical scheme is as follows: the phenol derivative monomer refers to one or a mixture of several compounds with the following chemical structures:
d \ Program Files (x86) \ gwssi \ CPC client \ cases \ inventions \ dbfdb876-bf66-453b-a1a8-5b5693e6051e \ new \100002\ dest _ path _ image010.jpg |
Wherein R5, R6, R7 and R8 each independently represent H, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group and a halogen atom; preferred are 2, 6-dimethylphenol, 2, 6-diethylphenol, 2, 6-di-n-propylphenol, 2, 6-diphenylphenol, 2, 6-xylylphenol, 2,3, 6-trimethylphenol, 2-methyl-6-ethylphenol, 2-methyl-6-propylphenol, 2-ethyl-6-bromophenol, 2-methyl-6-tolylphenol, 2-methyl-6-bromophenol and 2-ethyl-6-chlorophenol; more preferred are 2, 6-dimethylphenol, 2,3, 6-trimethylphenol and 2-methyl-6-bromophenol; most preferred is 2, 6-dimethylphenol;
the further preferred technical scheme is as follows: the catalyst is a metal salt-amine complex; the metal salt is one or a mixture of more of copper salt, manganese salt and chromium salt; preferred metal salts are copper halides, cuprous halides, cupric sulfate, cuprous sulfate, cupric nitrate, cuprous nitrate, cupric acetate, cuprous acetate, cupric propionate, cuprous propionate, cupric dodecanoate, cupric hexadecanoate, cuprous benzoate, and the corresponding manganese and chromium salts; besides the above metal salts, the corresponding metal salts or hydrates thereof can also be directly generated in the solution of the phenol derivative monomers by the reaction between copper, copper oxide, manganese oxide, chromium oxide, copper or manganese or chromium carbonate, copper or manganese or chromium hydroxide and organic acid or inorganic acid; preferred are cuprous halides;
the amine is one or a mixture of more of primary amine, secondary amine, tertiary amine, monoamine, diamine, polyamine and polymer with amino; preferred amines are dimethylamine, diethylamine, dipropylamine, dibutylamine, dibenzylamine, dicyclohexylamine, diethanolamine, methylethylamine, N-methylisopropylamine, N-methylcyclohexylamine, N-ethylisopropylamine, N-benzylmethylamine, N-benzyl-1-phenylethylamine, N-dimethylbutylamine, N-dialkylethylenediamine and pyridine;
the further preferred technical scheme is as follows: the solvent in the reaction liquid A and the reaction liquid B is one or a mixture of a plurality of organic solvents capable of dissolving the polyarylether resin and the catalyst, or a mixture of the organic solvents capable of dissolving the polyarylether resin and the catalyst and water; preferred are aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, methylene chloride and dichlorobenzene, nitroaromatic compounds such as nitrobenzene, aliphatic hydrocarbons and ethers; more preferred are aromatic hydrocarbons such as benzene, toluene, xylene, etc.; most preferred is toluene;
the further preferred technical scheme is as follows: the poor solvent is one or a mixture of more of alcohols such as methanol, ethanol, isopropanol and butanol, ketones such as acetone, butanone and methyl ethyl ketone, ether and ester; preferred are alcohols such as methanol, ethanol, isopropanol and butanol; most preferred is methanol.
The further preferred technical scheme is as follows: the modified resin is a terminal group modified hydrocarbon polymer, in particular to a terminal group modified polyarylether, polyolefin and one or a mixture of more of derivatives thereof; the end group is one or more of amido, hydroxyl and sulfydryl; the modified resin accounts for 0-50 wt% of the matrix resin;
the further preferred technical scheme is as follows: the main curing agent is epoxy resin, specifically is one or a mixture of more of bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol S epoxy resin, bisphenol F epoxy resin, dicyclopentadiene epoxy resin, naphthalene ring structure epoxy resin, biphenyl epoxy resin, heterocyclic epoxy resin, phenolic epoxy resin, organosilicon epoxy resin, polyfunctional group, aliphatic epoxy resin, cyanate ester modified epoxy resin and derivatives thereof, and accounts for 15-68 wt% of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit.
The further preferred technical scheme is as follows: the secondary curing agent is one or a mixture of more of active polyester, dihydric alcohol, polyhydric alcohol, diamine, polyamine, dithiol, polyhydric mercaptan, dihydric phenol, polyhydric phenol, phenolic resin, cyanate ester resin, anhydride, dicyandiamide, benzoxazine and derivatives thereof, and accounts for 0.1-12 wt% of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit;
the curing accelerator is one or a mixture of more of tertiary amine compounds, imidazole compounds, phosphine compounds, substituted urea compounds, phenol compounds and boron trifluoride amine complexes, and accounts for 0.02-5.0 wt% of the main curing agent;
the filler is SiO2、Al2O3、TiO2、ZnO、MgO、Bi2O3、AlN、Si3N4、SiC、BN、Al(OH)3、Mg(OH)2、BaTiO3、SrTiO3、Mg2TiO4、Bi2(TiO3)3、PbTiO3、NiTiO3、CaTiO3、ZnTiO3、Zn2TiO4、BaSnO3、Bi2(SnO3)3、CaSnO3、PbSnO3、MgSnO3、SrSnO3、ZnSnO3、BaZrO3、CaZrO3、PbZrO3、MgZrO3、SrZrO3、ZnZrO3One or a mixture of more of inorganic fillers such as graphite oxide, graphite fluoride, talcum powder, mica powder, kaolin, clay, solid glass beads, hollow glass beads, glass fibers, basalt fibers and carbon fibers, and also one or a mixture of more of organic fillers such as polytetrafluoroethylene pre-sintering materials, ultra-high molecular weight polyethylene fibers, Kevlar fibers, polyimide, polyetherimide, polyether ether ketone, polyphenylene sulfide and the like; the amount of the filler accounts for 0-80 wt% of the polyarylether-based composition containing the reversible thermal shrinkage and cold expansion structural unit;
the flame retardant is one or a mixture of more of aluminum-magnesium flame retardant, boron-zinc flame retardant, molybdenum-tin flame retardant, bromine flame retardant, antimony trioxide, phosphorus flame retardant, nitrogen flame retardant and derivatives thereof, and accounts for 1-50 wt% of the hydrocarbon composition.
A prepreg prepared by adopting the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit comprises the following specific preparation steps: preparing a uniform dispersion liquid of a polyarylether-based composition with a solid content of 35-75 wt/v% and containing reversible thermal shrinkage and cold expansion structural units, impregnating fiber cloth with the uniform dispersion liquid, and baking and drying to obtain a prepreg;
the solvent in the uniform dispersion liquid of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit is one of organic solvents or a mixture of a plurality of organic solvents which can be uniformly dispersed in the composition;
the fiber cloth is one of electronic grade alkali-free glass fiber cloth, carbon fiber, boron fiber, Kevlar, polyimide, polytetrafluoroethylene, polyester and the like;
the baking and drying are divided into two stages, wherein the baking and drying temperature of the first stage is 30-110 ℃, and the baking and drying temperature of the second stage is 110-180 ℃.
A thermosetting copper-clad plate prepared from the prepreg is prepared by the following steps in sequence: laminating the prepreg and the copper foil covered on the surface layer together to obtain the thermosetting copper-clad plate, wherein the number of the prepreg is more than or equal to 1, the number of the copper foil is 1 or 2, the laminating temperature is 130-280 ℃, and the laminating pressure is 80-130 kg/cm2The laminating time is 5min to 480 min.
The invention has wide application prospect.
Drawings
FIG. 1 is a GPC chart (THF phase) of a double-terminal hydroxyl group-containing polyphenylene ether resin containing a dibenzo eight-membered ring structural unit according to the present invention.
Detailed Description
The polyarylether-based composition containing reversible thermal shrinkage and cold expansion structural units and the prepreg and the thermosetting copper clad laminate prepared from the polyarylether-based composition are further described in detail by the following embodiments. However, this example is provided only as an illustration, and does not limit the present invention.
Examples 2 to 4
Adding 120 parts (by mol) of 2, 6-dimethylphenol into toluene, stirring, mixing and dissolving uniformly to obtain a reaction solution A with the concentration of 0.5mol/v per thousand; adding 1 part (mole) of copper bromide, 1 part (mole) of EDTA and 16 parts (mole) of monomer I into toluene, stirring, mixing and dissolving uniformly to obtain a reaction solution B with the concentration of the monomer I being 0.1mol/v per thousand; under the conditions that air is stably blown into the reaction liquid B, the mechanical stirring rotation speed is set to be 400rpm, and the oil bath temperature is 50 ℃, slowly dropwise adding the reaction liquid A into the reaction liquid B, and continuously stirring and reacting for 24 hours after dropwise adding is finished to obtain a product solution C; pouring the product solution C into a large amount of methanol for precipitation, performing operations such as filtration, methanol washing and the like for multiple times, and drying in a vacuum oven at 80 ℃ overnight to obtain the double-end hydroxyl type polyphenylene oxide resin containing the dibenzo eight-membered ring structural unit, wherein the GPC result is shown in the attached figure 1: number average molecular weight Mn =942, weight average molecular weight Mw = 1727.
Uniformly dispersing the matrix resin, the modified resin, the main curing agent, the secondary curing agent, the curing accelerator, the filler and the flame retardant in toluene, controlling the solid content of the dispersion liquid to be 60wt%, dipping 1080 glass fiber cloth in the uniform dispersion liquid, and baking to obtain the prepreg. The first stage baking and drying temperature is 60-100 ℃; the second stage baking and drying temperature is 100-170 ℃. And (3) superposing 8 prepregs, respectively attaching loz copper foils to two surfaces of each prepreg, and laminating for several hours under vacuum, pressurization and high temperature to obtain the copper-clad plate, wherein the specific formula is shown in the table below.
In 3 embodiments, the polyarylether based compositions containing reversible thermal shrinkage and cold expansion structural units all comprise double-end hydroxyl type polyarylether resin containing dibenzo eight-membered rings, modified resin, a main curing agent, a secondary curing agent, a curing accelerator, a filler and a flame retardant, and the specific formula is shown in the corresponding items in the table above, wherein the test performances of prepregs and copper clad plates are shown in the following.
Claims (10)
1. A polyarylether base composition containing reversible thermal shrinkage and cold expansion structural units is characterized in that: comprises seven components of matrix resin, modified resin, a main curing agent, a secondary curing agent, a curing accelerator, a filler and a flame retardant; the specific structure of the matrix resin is as follows:
wherein, R1, R2, R3 and R4 are any one of H, alkyl, substituted alkyl, aryl, substituted aryl and halogen atoms; a is more than or equal to 0; r is specifically one or a composite of two of the following structures:
the matrix resin accounts for 4-25 wt% of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit.
2. The polyarylether based composition containing reversible thermal shrinkage and cold expansion structural units according to claim 1, wherein: the specific preparation method of the matrix resin comprises the following steps:
step 1, adding a catalyst into a solution of a phenol derivative monomer, and uniformly stirring to obtain a reaction solution A; preparing a solution of a monomer I or a monomer II to obtain a reaction solution B; setting the reaction temperature to be 20-60 ℃, slowly dropwise adding the reaction liquid A into the reaction liquid B under the condition of introducing oxygen-containing gas while stirring, and continuously reacting for 4-72 hours after dropwise adding to obtain a product solution;
and 2, adding a poor solvent of the polyarylether resin into the product solution, uniformly stirring, standing until the polyarylether resin product is fully separated out and settled, and filtering, washing and drying to obtain the matrix resin.
3. The polyarylether based composition containing reversible thermal shrinkage and cold expansion structural units according to claim 2, wherein: the phenol derivative monomer refers to one or a mixture of several compounds with the following chemical structures:
wherein R5, R6, R7 and R8 are each any one of H, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group and a halogen atom.
4. The polyarylether based composition containing reversible thermal shrinkage and cold expansion structural units according to claim 2, wherein: the catalyst is a metal salt-amine complex; the metal salt is one or a mixture of more of copper salt, manganese salt and chromium salt; the amine is one or a mixture of several of primary amine, secondary amine, tertiary amine, monoamine, diamine, polyamine and polymer with amino.
5. The polyarylether based composition containing reversible thermal shrinkage and cold expansion structural units according to claim 2, wherein: the solvent in the reaction liquid A and the reaction liquid B is one or a mixture of more of organic solvents capable of dissolving the polyarylether resin and the catalyst, or a mixture of the organic solvents capable of dissolving the polyarylether resin and the catalyst and water.
6. The polyarylether based composition containing reversible thermal shrinkage and cold expansion structural units according to claim 2, wherein: the poor solvent is one or a mixture of more of methanol, ethanol, isopropanol, butanol, acetone, butanone, methyl ethyl ketone, ether and ester.
7. The polyarylether based composition containing reversible thermal shrinkage and cold expansion structural units according to claim 1, wherein: the modified resin is one or a mixture of a plurality of polyarylether and polyolefin modified by end groups; the end group is one or more of amido, hydroxyl and sulfydryl; the modified resin accounts for 0-50 wt% of the matrix resin;
the main curing agent is one or a mixture of more of bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol S epoxy resin, bisphenol F epoxy resin, dicyclopentadiene epoxy resin, naphthalene ring structure epoxy resin, biphenyl epoxy resin, heterocyclic epoxy resin, phenolic epoxy resin, organosilicon epoxy resin, polyfunctional groups, aliphatic epoxy resin and cyanate ester modified epoxy resin, and accounts for 15-68 wt% of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit.
8. The polyarylether based composition containing reversible thermal shrinkage and cold expansion structural units according to claim 1, wherein: the secondary curing agent is one or a mixture of more of active polyester, dihydric alcohol, polyhydric alcohol, diamine, polyamine, dithiol, polyhydric mercaptan, dihydric phenol, polyhydric phenol, phenolic resin, cyanate ester resin, anhydride, dicyandiamide and benzoxazine, and accounts for 0.1-12 wt% of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit;
the curing accelerator is one or a mixture of more of tertiary amine compounds, imidazole compounds, phosphine compounds, substituted urea compounds, phenol compounds and boron trifluoride amine complexes, and accounts for 0.02-5.0 wt% of the main curing agent;
the filler is SiO2、Al2O3、TiO2、ZnO、MgO、Bi2O3、AlN、Si3N4、SiC、BN、Al(OH)3、Mg(OH)2、BaTiO3、SrTiO3、Mg2TiO4、Bi2(TiO3)3、PbTiO3、NiTiO3、CaTiO3、ZnTiO3、Zn2TiO4、BaSnO3、Bi2(SnO3)3、CaSnO3、PbSnO3、MgSnO3、SrSnO3、ZnSnO3、BaZrO3、CaZrO3、PbZrO3、MgZrO3、SrZrO3、ZnZrO3One or a mixture of more of inorganic fillers such as graphite oxide, graphite fluoride, talcum powder, mica powder, kaolin, clay, solid glass beads, hollow glass beads, glass fibers, basalt fibers and carbon fibers, and also one or a mixture of more of polytetrafluoroethylene pre-sintering materials, ultra-high molecular weight polyethylene fibers, Kevlar fibers, polyimide, polyetherimide, polyether ether ketone and polyphenylene sulfide; the amount of the filler accounts for 0-80 wt% of the polyarylether-based composition containing the reversible thermal shrinkage and cold expansion structural unit;
the flame retardant is one or a mixture of more of an aluminum-magnesium flame retardant, a boron-zinc flame retardant, a molybdenum-tin flame retardant, a bromine flame retardant, antimony trioxide, a phosphorus flame retardant and a nitrogen flame retardant, and accounts for 1-50 wt% of the polyarylether-based composition containing the reversible thermal shrinkage and cold expansion structural unit.
9. A prepreg prepared by using the polyarylether-based composition containing the reversible thermal shrinkage and cold expansion structural unit as claimed in claim 1, which is characterized by comprising the following specific preparation steps: preparing a uniform dispersion liquid of a polyarylether-based composition with a solid content of 35-75 wt/v% and containing reversible thermal shrinkage and cold expansion structural units, impregnating fiber cloth with the uniform dispersion liquid, and baking and drying to obtain a prepreg;
the solvent in the uniform dispersion liquid of the polyarylether base composition containing the reversible thermal shrinkage and cold expansion structural unit is one of organic solvents or a mixture of a plurality of organic solvents which can be uniformly dispersed in the composition;
the fiber cloth is one of electronic grade alkali-free glass fiber cloth, carbon fiber, boron fiber, Kevlar, polyimide, polytetrafluoroethylene and polyester;
the baking and drying are divided into two stages, wherein the baking and drying temperature of the first stage is 30-110 ℃, and the baking and drying temperature of the second stage is 110-180 ℃.
10. The thermosetting copper-clad plate prepared by using the prepreg according to claim 9 is characterized by being prepared by the following steps in sequence: laminating the prepreg and the copper foil covering the surface layer of the prepreg together to obtain the thermosetting copper-clad plate through lamination, wherein the number of the prepregs is more than or equal to 1, the number of the copper foils is 1 or 2, the lamination temperature is 130-280 ℃, and the lamination pressure is 80-130 kg/cm2The laminating time is 5min to 480 min.
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| CN107163246A (en) * | 2017-05-20 | 2017-09-15 | 复旦大学 | Reversible thermal contraction polyarylamide of backbone chain type octatomic ring containing dibenzo structure and preparation method thereof |
| CN108659504A (en) * | 2018-05-17 | 2018-10-16 | 常州中英科技股份有限公司 | A kind of composition of cross-linking hydrocarbon polymer and its prepreg and the heat curing type copper-clad plate of preparation |
| CN109867914A (en) * | 2019-01-30 | 2019-06-11 | 常州中英科技股份有限公司 | A kind of hydrocarbon composition base prepreg of poly-dopamine modified lithium and its copper-clad plate of preparation |
| CN110605880A (en) * | 2019-08-07 | 2019-12-24 | 常州中英科技股份有限公司 | Thermosetting hydrocarbon polymer composition, prepreg prepared from thermosetting hydrocarbon polymer composition and thermosetting copper-clad plate |
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2020
- 2020-05-25 CN CN202010447844.6A patent/CN111534076A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107163246A (en) * | 2017-05-20 | 2017-09-15 | 复旦大学 | Reversible thermal contraction polyarylamide of backbone chain type octatomic ring containing dibenzo structure and preparation method thereof |
| CN108659504A (en) * | 2018-05-17 | 2018-10-16 | 常州中英科技股份有限公司 | A kind of composition of cross-linking hydrocarbon polymer and its prepreg and the heat curing type copper-clad plate of preparation |
| CN109867914A (en) * | 2019-01-30 | 2019-06-11 | 常州中英科技股份有限公司 | A kind of hydrocarbon composition base prepreg of poly-dopamine modified lithium and its copper-clad plate of preparation |
| CN110605880A (en) * | 2019-08-07 | 2019-12-24 | 常州中英科技股份有限公司 | Thermosetting hydrocarbon polymer composition, prepreg prepared from thermosetting hydrocarbon polymer composition and thermosetting copper-clad plate |
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