TW202200662A - 酚樹脂、環氧樹脂、該些的製造方法、環氧樹脂組成物、預浸體、積層板、印刷配線基板及硬化物 - Google Patents
酚樹脂、環氧樹脂、該些的製造方法、環氧樹脂組成物、預浸體、積層板、印刷配線基板及硬化物 Download PDFInfo
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- TW202200662A TW202200662A TW110120916A TW110120916A TW202200662A TW 202200662 A TW202200662 A TW 202200662A TW 110120916 A TW110120916 A TW 110120916A TW 110120916 A TW110120916 A TW 110120916A TW 202200662 A TW202200662 A TW 202200662A
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- Prior art keywords
- epoxy resin
- phenol
- parts
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- resin
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 168
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 168
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 110
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 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 36
- 239000004848 polyfunctional curative Substances 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 15
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000002841 Lewis acid Substances 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229920005989 resin Polymers 0.000 abstract description 57
- 239000011347 resin Substances 0.000 abstract description 57
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 12
- 239000011889 copper foil Substances 0.000 abstract description 11
- 239000011229 interlayer Substances 0.000 abstract description 10
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- 239000000853 adhesive Substances 0.000 abstract description 4
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 abstract 2
- -1 methylcyclohexyl Chemical group 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 31
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- 238000005227 gel permeation chromatography Methods 0.000 description 27
- 229920003986 novolac Polymers 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 25
- 150000002989 phenols Chemical class 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 23
- 238000010438 heat treatment Methods 0.000 description 20
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 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 17
- 239000003063 flame retardant Substances 0.000 description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
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- 150000002148 esters Chemical class 0.000 description 15
- 229910052698 phosphorus Inorganic materials 0.000 description 15
- 239000011574 phosphorus Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 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 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229930185605 Bisphenol Natural products 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 12
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 12
- 235000011116 calcium hydroxide Nutrition 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 10
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- 230000018044 dehydration Effects 0.000 description 10
- 238000006297 dehydration reaction Methods 0.000 description 10
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000920 calcium hydroxide Substances 0.000 description 9
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 9
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 9
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 235000013824 polyphenols Nutrition 0.000 description 9
- 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 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 229930003836 cresol Natural products 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000003825 pressing Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 150000004780 naphthols Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002994 raw material Substances 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
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- 239000007788 liquid Substances 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
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- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
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- 239000004643 cyanate ester Substances 0.000 description 5
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- 239000000945 filler Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 5
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- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
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- 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 4
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- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 3
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
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- 125000001624 naphthyl group Chemical group 0.000 description 3
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 2
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- XXKHDSGLCLCFSC-UHFFFAOYSA-N 2,3-diphenylphenol Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C1=CC=CC=C1 XXKHDSGLCLCFSC-UHFFFAOYSA-N 0.000 description 2
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- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
本發明是有關於一種低介電特性及高接著性優異的酚樹脂或環氧樹脂及其製造方法。
環氧樹脂由於接著性、可撓性、耐熱性、耐化學品性、絕緣性、硬化反應性優異,因此於塗料、土木接著、注塑、電氣電子材料、膜材料等多方面中使用。尤其於作為電氣電子材料之一的印刷配線基板用途中,藉由對環氧樹脂賦予阻燃性而得到廣泛使用。
近年來,資訊設備的小型化、高性能化正在急速發展,與此相伴,對半導體或電子零件的領域中使用的材料,要求較以往更高的性能。尤其對於作為電氣電子零件的材料的環氧樹脂組成物,要求伴隨基板的薄型化及高功能化的低介電特性。
迄今為止,於積層板用途的低介電常數化中,一直使用導入有脂肪族骨架的二環戊二烯酚樹脂等,但於改善介電損耗正切方面效果不足,關於接著性,亦無法令人滿意。另外,尚未公開有於苯酚環上取代有多個源自二環戊二烯的二環戊烯基的樹脂(專利文獻1、專利文獻2)。
[現有技術文獻]
[專利文獻]
[專利文獻1]日本專利特開2001-240654號公報
[專利文獻2]日本專利特開平5-339341號公報
因此,本發明所欲解決之課題在於提供一種可獲得表現出優異的介電損耗正切、接著性亦良好的硬化物的二環戊二烯型酚樹脂及二環戊二烯型環氧樹脂、使用該些的環氧樹脂組成物、以及該些的製造方法。
為解決所述課題,本發明者等人研究了二環戊二烯型酚樹脂的製造方法,結果發現,藉由使二環戊二烯型酚樹脂進而與特定比率的二環戊二烯反應,可於二環戊二烯型酚樹脂的苯酚環上加成源自二環戊二烯的二環戊烯基,進而於使將該酚樹脂環氧化時獲得的環氧樹脂與硬化劑硬化時,所獲得的硬化物的低介電特性及接著性優異,從而完成本發明。
即,本發明是一種由下述通式(1)所表示且含有二環戊烯基的酚樹脂。
[化1](1)
此處,R1
獨立地表示碳數1~8的烴基。R2
獨立地表示氫原子或二環戊烯基,且至少一個為二環戊烯基。i為0~2的整數。n表示重複數,其平均值為0~10的數。
所述R1
較佳為甲基或苯基,所述i較佳為1或2。
另外,本發明是一種所述含有二環戊烯基的酚樹脂的製造方法,其特徵在於,於路易斯酸的存在下,相對於下述通式(3)所表示的酚樹脂的酚性羥基1莫耳,使0.05莫耳~2.0莫耳的二環戊二烯於50℃~200℃的反應溫度下進行反應。
[化2](3)
此處,R1
及i與所述通式(1)中的定義同義。m表示重複數,其平均值為0~5的數。
較佳為相對於所述二環戊二烯100質量份,使用0.001質量份~20質量份的路易斯酸。
另外,本發明是一種所述含有二環戊烯基的環氧樹脂的製造方法,其特徵在於,相對於所述含有二環戊烯基的酚樹脂的酚性羥基1莫耳,使1莫耳~20莫耳的表鹵醇於鹼金屬氫氧化物的存在下進行反應。
另外,本發明是一種環氧樹脂組成物,其是含有環氧樹脂及硬化劑的環氧樹脂組成物,其特徵在於,以所述含有二環戊烯基的酚樹脂及/或環氧樹脂為必需成分。
另外,本發明是一種使所述環氧樹脂組成物硬化而成的硬化物,是一種使用所述環氧樹脂組成物的預浸體、積層板或印刷配線基板。
本發明的製造方法可容易地於二環戊二烯型酚樹脂的苯酚環上加成源自二環戊二烯的二環戊烯基。另外,使用藉由該製造方法而獲得的酚樹脂及/或環氧樹脂的硬化物可提供顯現出優異的介電損耗正切、進而於印刷配線板用途中銅箔剝離強度及層間密接強度優異的環氧樹脂組成物。
以下,對本發明的實施方式進行詳細說明。
本發明的酚樹脂是由所述通式(1)所表示且含有二環戊烯基的酚樹脂。該樹脂例如是於路易斯酸的存在下,使二環戊二烯與所述通式(3)所表示的二環戊二烯型酚樹脂反應而獲得。
此處,通式(3)所表示的二環戊二烯型酚樹脂具有由二環戊二烯將酚類連結的結構。本發明的通式(1)所表示的酚樹脂是於式(3)的二環戊二烯型酚樹脂中,進而於苯酚環上加成二環戊二烯而作為取代基(R2
)存在者。
通式(1)中,R1
表示碳數1~8的烴基。較佳為碳數1~8的烷基、碳數6~8的芳基、碳數7~8的芳烷基或烯丙基。作為碳數1~8的烷基,可為直鏈狀、分支狀、環狀的任一種,例如可列舉甲基、乙基、丙基、異丙基、正丁基、第三丁基、己基、環己基、甲基環己基等,但並不限定於該些。作為碳數6~8的芳基,可列舉苯基、甲苯基、二甲苯基、乙基苯基等,但並不限定於該些。作為碳數7~8的芳烷基,可列舉苄基、α-甲基苄基等,但並不限定於該些。該些取代基中,就獲取的容易性及製成硬化物時的反應性的觀點而言,較佳為苯基、甲基,特佳為甲基。R1
的取代位置可為正位、間位、對位中的任一種,但較佳為正位。
i為取代基R1
的個數,為0~2,較佳為1~2。
R2
獨立地表示氫原子或二環戊烯基,至少一個為二環戊烯基。二環戊烯基是源自二環戊二烯的基,由下述式(1a)或式(1b)所表示。由於該基的存在,含有本發明的酚樹脂或其環氧樹脂而成的樹脂組成物的硬化物可降低介電常數、介電損耗正切。
[化4](1a)(1b)
n為重複數,表示0以上的數,其平均值(數量平均)為0~10,較佳為1.0~5.0,更佳為1.2~4.0,進而佳為1.3~3.5。
作為藉由GPC而得的含量,較佳為n=0體為10面積%以下,n=1體為20面積%~70面積%,n=2體以上為20面積%~80面積%的範圍內。
關於本發明的酚樹脂的分子量,重量平均分子量(Mw)較佳為400~2000,更佳為500~1500,進而佳為600~1400,數量平均分子量(Mn)較佳為350~1500,更佳為400~1000,進而佳為500~800。
酚性羥基當量(g/eq.)較佳為190~500,更佳為220~500,進而佳為250~400。
軟化點較佳為80℃~180℃,更佳為90℃~160℃。
通式(3)中,R1
及i與所述通式(1)中的定義同義。
m為重複數,表示0以上的數,其平均值(數量平均)為0~5,較佳為1.0~4.0,更佳為1.1~3.0,進而佳為1.2~2.5。
於通式(3)所表示的二環戊二烯型酚樹脂中,酚性羥基當量(g/eq.)較佳為150~250,更佳為160~220,進而佳為170~210。
作為藉由GPC而得的含量,較佳為m=0體為10面積%以下,m=1體為50面積%~90面積%,m=2體以上為10面積%~50面積%的範圍內。
作為所述通式(4)所表示的酚類,可列舉:苯酚、甲酚、乙基苯酚、丙基苯酚、異丙基苯酚、正丁基苯酚、第三丁基苯酚、己基苯酚、環己基苯酚、苯基苯酚、甲苯基苯酚、苄基苯酚、α-甲基苄基苯酚、烯丙基苯酚、二甲基苯酚、二乙基苯酚、二丙基苯酚、二異丙基苯酚、二(正丁基)苯酚、二(第三丁基)苯酚、二己基苯酚、二環己基苯酚、二苯基苯酚、二甲苯基苯酚、二苄基苯酚、雙(α-甲基苄基)苯酚、甲基乙基苯酚、甲基丙基苯酚、甲基異丙基苯酚、甲基丁基苯酚、甲基第三丁基苯酚、甲基烯丙基苯酚、甲苯基苯基苯酚等。就獲得容易性及製成硬化物時的反應性的觀點而言,較佳為苯酚、甲酚、苯基苯酚、二甲基苯酚、二苯基苯酚,特佳為甲酚、二甲基苯酚。
所述反應中使用的觸媒為路易斯酸,具體而言為三氟化硼、三氟化硼-酚錯合物、三氟化硼-醚錯合物、氯化鋁、氯化錫、氯化鋅、氯化鐵等,其中,就操作的容易度而言,較佳為三氟化硼-醚錯合物。於三氟化硼-醚錯合物的情況下,相對於二環戊二烯100質量份,觸媒的使用量為0.001質量份~20質量份,較佳為0.5質量份~10質量份。
關於所述反應中的酚類與二環戊二烯的比率,相對於酚類1莫耳,二環戊二烯為0.08莫耳~0.80莫耳,較佳為0.09莫耳~0.60莫耳,更佳為0.10莫耳~0.50莫耳,進而佳為0.11莫耳~0.40莫耳,特佳為0.11莫耳~0.20莫耳。
該反應適宜為將酚類及觸媒裝入反應器中,歷時0.1小時~10小時、較佳為0.5小時~8小時、更佳為1小時~6小時滴加二環戊二烯的方式。
反應溫度較佳為50℃~200℃,更佳為100℃~180℃,進而佳為120℃~160℃。反應時間較佳為1小時~10小時,更佳為3小時~10小時,進而佳為4小時~8小時。
反應結束後,加入氫氧化鈉、氫氧化鉀、氫氧化鈣等鹼使觸媒失活。其後,加入甲苯、二甲苯等芳香族烴類或甲基乙基酮、甲基異丁基酮等酮類等的溶劑加以溶解,水洗後,於減壓下回收溶劑,藉此可獲得作為目標的通式(3)所表示的二環戊二烯酚樹脂。再者,較佳為使二環戊二烯儘可能全部反應,並將未反應的原料酚類減壓回收。
反應時,根據需要亦可使用苯、甲苯、二甲苯等芳香族烴類,或甲基乙基酮、甲基異丁基酮等酮類,氯苯、二氯苯等鹵化烴類,或乙二醇二甲醚、二乙二醇二甲醚等醚類等的溶劑。
作為用於向通式(3)所表示的二環戊二烯型酚樹脂中導入所述式(1a)或式(1b)的二環戊烯基結構的反應方法,是相對於所述二環戊二烯酚樹脂,使二環戊二烯以規定的比率反應的方法。關於反應比率,相對於二環戊二烯酚樹脂的酚性羥基1莫耳,二環戊二烯為0.05莫耳~2.0莫耳,更佳為0.1莫耳~1.0莫耳,進而佳為0.15莫耳~0.80莫耳,特佳為0.30莫耳~0.70莫耳。
所述反應中使用的觸媒為路易斯酸,具體而言為三氟化硼、三氟化硼-酚錯合物、三氟化硼-醚錯合物、氯化鋁、氯化錫、氯化鋅、氯化鐵等,其中,就操作的容易度而言,較佳為三氟化硼-醚錯合物。於三氟化硼-醚錯合物的情況下,相對於二環戊二烯100質量份,觸媒的使用量為0.001質量份~20質量份,較佳為0.5質量份~10質量份。
該反應適宜為將二環戊二烯酚樹脂、觸媒及溶劑裝入反應器中,溶解後,歷時0.1小時~10小時、較佳為0.5小時~8小時、更佳為1小時~6小時滴加二環戊二烯的方式。
反應溫度較佳為50℃~200℃,更佳為100℃~180℃,進而佳為120℃~160℃。反應時間較佳為1小時~10小時,更佳為3小時~10小時,進而佳為4小時~8小時。
反應結束後,加入氫氧化鈉、氫氧化鉀、氫氧化鈣等鹼使觸媒失活。其後,加入甲苯、二甲苯等芳香族烴類或甲基乙基酮、甲基異丁基酮等酮類等的溶劑加以溶解,水洗後,於減壓下回收溶劑,藉此可獲得作為目標的酚樹脂。
反應時使用的溶劑可列舉苯、甲苯、二甲苯等芳香族烴類,或甲基乙基酮、甲基異丁基酮等酮類,氯苯、二氯苯等鹵化烴類,或乙二醇二甲醚、二乙二醇二甲醚等醚類等的溶劑。該些溶劑可單獨使用,亦可混合使用兩種以上。
作為確認於本發明的酚樹脂中導入有式(1a)或式(1b)所表示的取代基(二環戊烯基)的方法,可使用質量分析法及傅立葉轉換紅外光譜(Fourier transform infrared spectroscopy,FT-IR)測定。
於使用質量分析方法的情況下,可使用電灑質量分析法(電灑游離質譜法(electrospray ionization mass spectrometry,ESI-MS))或場脫附法(場脫附質譜(field desorption mass spectrometry,FD-MS))等。藉由對利用GPC等將核體數不同的成分分離所得的樣品實施質量分析法,可確認導入有式(1a)或式(1b)所表示的取代基。
於使用FT-IR測定法的情況下,將溶解於四氫呋喃(tetrahydrofuran,THF)等有機溶劑中的樣品塗佈於KRS-5單元上,利用FT-IR來測定使有機溶劑乾燥而獲得的帶樣品薄膜的單元時,由苯酚核的C-O伸縮振動引起的波峰出現在1210 cm-1
附近,僅於導入有式(1a)或式(1b)的情況下,在3040 cm-1
附近出現由二環戊烯基骨架的烯烴部位的C-H伸縮振動引起的波峰。順帶而言,作為酚類彼此的連結基的二環戊烯基並非烯烴,因此未出現該吸收波峰。
當將以直線形式連接目標波峰的起點與終點而得者設為基線、將自波峰的頂點至基線的長度設為峰高時,根據3040 cm-1
附近的波峰(A3040
)與1210 cm-1
附近的波峰(A1210
)的比率(A3040
/A1210
),可確定式(1a)或式(1b)的導入量。可確認到其比率越大物性值越良好,用以滿足目標物性的較佳比率(A3040
/A1210
)為0.05以上,更佳為0.10以上,進而佳為0.15以上。上限值並無特別限定,例如為0.50左右。
本發明的環氧樹脂由所述通式(2)所表示。該環氧樹脂是藉由使表氯醇(epichlorohydrin)等表鹵醇與所述通式(1)所表示的酚樹脂反應而獲得。該反應依照現有公知的方法進行。
通式(2)中,R1
、R2
及i與所述通式(1)的定義同義。
k為重複數,表示0以上的數,以其平均值(數量平均)計為0~10,較佳為1.0~5.0,更佳為1.2~4.0,進而佳為1.3~3.5。
作為環氧化的方法,例如可藉由以下方式來獲得:於酚樹脂與相對於酚樹脂的羥基為過量莫耳的表鹵醇的混合物中,以固體或濃稠水溶液的形式加入氫氧化鈉等鹼金屬氫氧化物,於30℃~120℃的反應溫度下使其反應0.5小時~10小時,或者於酚樹脂與過量莫耳量的表鹵醇中加入四乙基氯化銨等四級銨鹽作為觸媒,於50℃~150℃的溫度下反應1小時~5小時,並於所得的聚鹵醇醚(polyhalohydrin ether)中以固體或濃稠水溶液的形式加入氫氧化鈉等鹼金屬氫氧化物,於30℃~120℃的溫度下使其反應1小時~10小時。
於所述反應中,相對於酚樹脂的羥基,表鹵醇的使用量為1倍莫耳~20倍莫耳,較佳為2倍莫耳~8倍莫耳。另外,相對於酚樹脂的羥基,鹼金屬氫氧化物的使用量為0.85倍莫耳~1.15倍莫耳。
由於該些反應中得到的環氧樹脂含有未反應的表鹵醇及鹼金屬的鹵化物,故可自反應混合物中蒸發除去未反應的表鹵醇,進而藉由利用水進行萃取、過濾等的方法除去鹼金屬的鹵化物,從而獲得目標環氧樹脂。
本發明的環氧樹脂的環氧當量(g/eq.)較佳為200~4000,更佳為220~2000,進而佳為250~700。特別是於使用二氰二胺(dicyandiamide)作為硬化劑的情況下,為了防止於預浸體上析出二氰二胺的結晶,環氧當量較佳為300以上。
作為藉由GPC而得的含量,較佳為k=0體為10面積%以下,k=1體為10面積%~70面積%,k=2體以上為30面積%~80面積%的範圍內。
總氯含量較佳為2000 ppm以下,進而佳為1500 ppm以下。
藉由本發明的製造方法而獲得的環氧樹脂的分子量分佈能夠藉由變更環氧化反應時的酚樹脂與表鹵醇的裝入比率來變更,表鹵醇的使用量相對於酚樹脂的羥基越接近等莫耳則成為高分子量分佈,越接近20莫耳倍則成為低分子量分佈。另外,對於所獲得的環氧樹脂,藉由再次使酚樹脂起作用,亦能夠使其高分子量化。
藉由使用所述本發明的酚樹脂及/或本發明的環氧樹脂,可獲得本發明的環氧樹脂組成物。本發明的環氧樹脂組成物以環氧樹脂及硬化劑為必需成分。作為該實施方式,硬化劑為本發明的酚樹脂及/或環氧樹脂為本發明的環氧樹脂。
較佳為硬化劑中至少30質量%為所述通式(1)所表示的酚樹脂,或者環氧樹脂中至少30質量%為所述通式(2)所表示的環氧樹脂,更佳為含有50質量%以上。於較其更少的情況下,有介電特性惡化之虞。
換言之,於硬化劑的30質量%以上為本發明的酚樹脂的情況下,環氧樹脂無需為本發明的環氧樹脂,於本發明的酚樹脂未滿硬化劑的30質量%的情況下,環氧樹脂的30質量%以上必須為本發明的環氧樹脂。
作為為了獲得本發明的環氧樹脂組成物而使用的環氧樹脂,可根據需要併用一種或兩種以上的各種環氧樹脂。
作為可併用的環氧樹脂,分子中具有兩個以上的環氧基的通常的環氧樹脂皆可使用。若舉例,則可列舉:雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚AF型環氧樹脂、四甲基雙酚F型環氧樹脂、對苯二酚型環氧樹脂、聯苯型環氧樹脂、二苯乙烯型環氧樹脂、雙酚芴型環氧樹脂、雙酚S型環氧樹脂、雙硫醚型環氧樹脂、間苯二酚型環氧樹脂、聯苯基芳烷基酚型環氧樹脂、萘二酚型環氧樹脂、苯酚酚醛清漆型環氧樹脂、芳香族改質苯酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、烷基酚醛清漆型環氧樹脂、雙酚酚醛清漆型環氧樹脂、聯萘酚型環氧樹脂、萘酚酚醛清漆型環氧樹脂、β-萘酚芳烷基型環氧樹脂、二萘酚芳烷基型環氧樹脂、α-萘酚芳烷基型環氧樹脂、三苯基甲烷型環氧樹脂等三官能環氧樹脂、四苯基乙烷型環氧樹脂等四官能環氧樹脂、本發明以外的二環戊二烯型環氧樹脂、1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、甘油聚縮水甘油醚、三羥甲基丙烷聚縮水甘油醚、三羥甲基乙烷聚縮水甘油醚、季戊四醇聚縮水甘油醚等多元醇聚縮水甘油醚、丙二醇二縮水甘油醚等烷二醇型環氧樹脂、環己烷二甲醇二縮水甘油醚等脂肪族環狀環氧樹脂、二聚酸聚縮水甘油酯等縮水甘油酯類、苯基二縮水甘油胺、三-二縮水甘油胺、二胺基二苯基甲烷四縮水甘油胺、胺基苯酚型環氧樹脂等縮水甘油胺型環氧樹脂、賽羅西德(Celloxide)2021P(大賽璐(Daicel)股份有限公司製造)等脂環式環氧樹脂、含磷環氧樹脂、含溴環氧樹脂、胺基甲酸酯改質環氧樹脂、含噁唑啶酮環的環氧樹脂等,但並不限定於該些。另外,該些環氧樹脂可單獨使用,亦可併用兩種以上。就獲取容易度的觀點而言,進而佳為使用下述通式(5)所表示的環氧樹脂、或本發明以外的二環戊二烯型環氧樹脂、萘二酚型環氧樹脂、苯酚酚醛清漆型環氧樹脂、芳香族改質苯酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、α-萘酚芳烷基型環氧樹脂、二環戊二烯型環氧樹脂、含磷環氧樹脂、含噁唑啶酮環的環氧樹脂。
[化6](5)(5a)
此處,R3
獨立地表示碳數1~8的烴基,例如為甲基、乙基、正丙基、異丙基、正丁基、第三丁基、正己基、環己基等烷基,彼此可相同亦可不同。
X表示二價有機基,例如表示亞甲基、伸乙基、伸異丙基、伸異丁基、六氟伸異丙基等伸烷基、-CO-、-O-、-S-、-SO2
-、-S-S-、或式(5a)所表示的伸烷基。
R4
獨立地表示氫原子或碳數1以上的烴基,例如為甲基,彼此可相同亦可不同。
Ar為苯環或萘環,該些苯環或萘環可具有碳數1~10的烷基、碳數1~10的烷氧基、碳數6~11的芳基、碳數7~12的芳烷基、碳數6~11的芳氧基、或碳數7~12的芳烷基氧基作為取代基。
作為硬化劑,除所述通式(1)的多元羥基樹脂以外,根據需要亦可併用一種或兩種以上的各種酚樹脂類、酸酐類、胺類、氰酸酯類、活性酯類、醯肼類、酸性聚酯類、芳香族氰酸酯類等通常使用的硬化劑。於併用該些硬化劑的情況下,所併用的硬化劑較佳為全部硬化劑中的70質量%以下,更佳為50質量%以下。若所併用的硬化劑的比例過多,則作為環氧樹脂組成物的介電特性及接著特性有惡化之虞。
於本發明的環氧樹脂組成物中,相對於全部環氧樹脂的環氧基1莫耳,硬化劑的活性氫基的莫耳比較佳為0.2莫耳~1.5莫耳,更佳為0.3莫耳~1.4莫耳,進而佳為0.5莫耳~1.3莫耳,特佳為0.8莫耳~1.2莫耳。於超出該範圍的情況下,有硬化不完全而無法獲得良好的硬化物性之虞。例如,於使用酚樹脂系硬化劑或胺系硬化劑的情況下,相對於環氧基而調配大致等莫耳的活性氫基。於使用酸酐系硬化劑的情況下,相對於環氧基1莫耳而調配0.5莫耳~1.2莫耳、較佳為0.6莫耳~1.0莫耳的酸酐基。於單獨使用本發明的酚樹脂作為硬化劑的情況下,相對於環氧樹脂1莫耳,理想為以0.9莫耳~1.1莫耳的範圍使用。
本發明中所謂活性氫基是具有與環氧基具有反應性的活性氫的官能基(包含具有因水解等而產生活性氫的潛在性活性氫的官能基、或顯示同等的硬化作用的官能基),具體而言可列舉酸酐基或羧基或胺基或酚性羥基等。再者,關於活性氫基,1莫耳的羧基或酚性羥基算為1莫耳,胺基(NH2
)算為2莫耳。另外,於活性氫基並不明確的情況下,可藉由測定而求出活性氫當量。例如,可使環氧當量已知的苯基縮水甘油醚等單環氧樹脂與活性氫當量未知的硬化劑反應,測定所消耗的單環氧樹脂的量,藉此求出所使用的硬化劑的活性氫當量。
作為本發明的環氧樹脂組成物中可使用的酚樹脂系硬化劑,具體例可列舉:雙酚A、雙酚F、雙酚C、雙酚K、雙酚Z、雙酚S、四甲基雙酚A、四甲基雙酚F、四甲基雙酚S、四甲基雙酚Z、四溴雙酚A、二羥基二苯硫醚、4,4'-硫代雙(3-甲基-6-第三丁基苯酚)等雙酚類,或兒茶酚、雷瑣辛(resorcin)、甲基雷瑣辛、對苯二酚、單甲基對苯二酚、二甲基對苯二酚、三甲基對苯二酚、單-第三丁基對苯二酚、二-第三丁基對苯二酚等二羥基苯類,或二羥基萘、二羥基甲基萘、二羥基甲基萘、三羥基萘等羥基萘類,或LC-950PM60(新安(Shin-AT&C)公司製造)等含磷酚硬化劑,或昭能(Shonol)BRG-555(愛克工業(Aica Kogyo)股份有限公司製造)等苯酚酚醛清漆樹脂、DC-5(日鐵化學&材料股份有限公司製造)等甲酚酚醛清漆樹脂、含三嗪骨架的酚樹脂、芳香族改質苯酚酚醛清漆樹脂、雙酚A酚醛清漆樹脂、樂吉拓(Resitop)TPM-100(群榮化學工業股份有限公司製造)等三羥基苯基甲烷型酚醛清漆樹脂、萘酚酚醛清漆樹脂等苯酚類、萘酚類及/或雙酚類與醛類的縮合物,SN-160、SN-395、SN-485(日鐵化學&材料股份有限公司製造)等苯酚類、苯酚類及/或萘酚類及/或雙酚類與伸二甲苯基二醇的縮合物,苯酚類及/或萘酚類與異丙烯基苯乙酮的縮合物,苯酚類及/或萘酚類及/或雙酚類與二環戊二烯的反應產物,苯酚類及/或萘酚類及/或雙酚類與二乙烯基苯的反應產物,苯酚類及/或萘酚類及/或雙酚類與萜烯類的反應產物,苯酚類及/或萘酚類及/或雙酚類與聯苯系交聯劑的縮合物等所謂的被稱為酚醛清漆酚樹脂的酚化合物、聚丁二烯改質酚樹脂、具有螺環的酚樹脂等。就獲取容易度的觀點而言,較佳為苯酚酚醛清漆樹脂、二環戊二烯酚樹脂、三羥基苯基甲烷型酚醛清漆樹脂、芳香族改質苯酚酚醛清漆樹脂等。
酚醛清漆酚樹脂可由酚類與交聯劑獲得。作為苯酚類,可列舉苯酚、甲酚、二甲酚、丁基苯酚、戊基苯酚、壬基苯酚、丁基甲基苯酚、三甲基苯酚、苯基苯酚等,作為萘酚類,可列舉1-萘酚、2-萘酚等,此外亦可列舉作為所述酚樹脂系硬化劑而列舉的雙酚類。作為用作交聯劑的醛類,可例示甲醛、乙醛、丙醛、丁醛、戊醛、己醛、苯甲醛、氯醛、溴醛、乙二醛、丙二醛、丁二醛、戊二醛、己二醛、庚二醛、癸二醛、丙烯醛、巴豆醛、柳醛、鄰苯二甲醛、羥基苯甲醛等。作為聯苯系交聯劑,可列舉雙(羥甲基)聯苯、雙(甲氧基甲基)聯苯、雙(乙氧基甲基)聯苯、雙(氯甲基)聯苯等。
作為酸酐系硬化劑,具體而言可列舉:馬來酸酐、甲基四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、4-甲基六氫鄰苯二甲酸酐、甲基雙環[2.2.1]庚烷-2,3-二羧酸酐、雙環[2.2.1]庚烷-2,3-二羧酸酐、1,2,3,6-四氫鄰苯二甲酸酐、均苯四甲酸酐、鄰苯二甲酸酐、偏苯三甲酸酐、甲基納迪克酸、苯乙烯單體與馬來酸酐的共聚物、茚類與馬來酸酐的共聚物等。
作為胺系硬化劑,具體而言可列舉:二乙三胺、三乙四胺、間苯二甲胺、異佛爾酮二胺、二胺基二苯基甲烷、二胺基二苯基碸、二胺基二苯基醚、苄基二甲胺、2,4,6-三(二甲基胺基甲基)苯酚、聚醚胺、雙胍化合物、二氰二胺、甲氧苯胺(anisidine)等芳香族胺類、作為二聚酸等酸類與多胺類的縮合物的聚醯胺胺等胺系化合物等。
作為氰酸酯化合物,只要是一分子中具有兩個以上的氰酸基(氰酸酯基)的化合物則並無特別限定。例如,可列舉:苯酚酚醛清漆型、烷基苯酚酚醛清漆型等酚醛清漆型氰酸酯系硬化劑,萘酚芳烷基型氰酸酯系硬化劑,聯苯烷基型氰酸酯系硬化劑,二環戊二烯型氰酸酯系硬化劑,雙酚A型、雙酚F型、雙酚E型、四甲基雙酚F型、雙酚S型等雙酚型氰酸酯系硬化劑,以及該些的一部分三嗪化的預聚物等。作為氰酸酯系硬化劑的具體例,例如可列舉:雙酚A二氰酸酯、多酚氰酸酯(寡聚(3-亞甲基-1,5-伸苯基氰酸酯)、雙(3-甲基-4-氰酸酯苯基)甲烷、雙(3-乙基-4-氰酸酯苯基)甲烷、雙(4-氰酸酯苯基)-1,1-乙烷、4,4-二氰酸酯-二苯基酯、2,2-雙(4-氰酸酯苯基)-1,1,1,3,3,3-六氟丙烷、4,4'-亞甲基雙(2,6-二甲基苯基氰酸酯)、4,4'-亞乙基二苯基二氰酸酯、六氟雙酚A二氰酸酯、2,2-雙(4-氰酸酯)苯基丙烷、1,1-雙(4-氰酸酯苯基甲烷)、雙(4-氰酸酯-3,5-二甲基苯基)甲烷、1,3-雙(4-氰酸酯苯基-1-(甲基亞乙基))苯、雙(4-氰酸酯苯基)硫醚、雙(4-氰酸酯苯基)醚等二官能氰酸酯樹脂,三(4-氰酸酯苯基)-1,1,1-乙烷、雙(3,5-二甲基-4-氰酸酯苯基)-4-氰酸酯苯基-1,1,1-乙烷等三元酚的氰酸酯,自苯酚酚醛清漆、甲酚酚醛清漆、含二環戊二烯結構的酚樹脂等衍生的多官能氰酸酯樹脂、該些氰酸酯樹脂的一部分三嗪化的預聚物等。該些可使用一種或兩種以上。
作為活性酯系硬化劑,並無特別限制,但一般較佳為使用苯酚酯類、苯硫酚酯類、N-羥基胺酯類、雜環羥基化合物的酯類等於一分子中具有兩個以上的反應活性高的酯基的化合物。該活性酯系硬化劑較佳為藉由羧酸化合物及/或硫代羧酸化合物與羥基化合物及/或硫醇化合物的縮合反應而獲得。特別是就耐熱性提高的觀點而言,較佳為由羧酸化合物與羥基化合物獲得的活性酯系硬化劑,更佳為由羧酸化合物與苯酚化合物及/或萘酚化合物獲得的活性酯系硬化劑。作為羧酸化合物,例如可列舉苯甲酸、乙酸、琥珀酸、馬來酸、衣康酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、均苯四甲酸等。作為苯酚化合物或萘酚化合物,例如可列舉:對苯二酚、間苯二酚、雙酚A、雙酚F、雙酚S、酸式酚酞(phenolphthalin)、甲基化雙酚A、甲基化雙酚F、甲基化雙酚S、苯酚、鄰甲酚、間甲酚、對甲酚、兒茶酚、α-萘酚、β-萘酚、1,5-二羥基萘、1,6-二羥基萘、2,6-二羥基萘、二羥基二苯甲酮、三羥基二苯甲酮、四羥基二苯甲酮、間苯三酚(phloroglucin)、苯三酚、二環戊二烯基二苯酚、作為本發明的環氧樹脂的前驅物的二環戊二烯酚樹脂、苯酚酚醛清漆等。活性酯系硬化劑可使用一種或兩種以上。作為活性酯系硬化劑,具體而言較佳為包含二環戊二烯基二苯酚結構的活性酯系硬化劑、包含萘結構的活性酯系硬化劑、作為苯酚酚醛清漆的乙醯基化物的活性酯系硬化劑、作為苯酚酚醛清漆的苯甲醯基化物的活性酯系硬化劑等,其中,就剝離強度的提高優異的方面而言,更佳為包含本發明的環氧樹脂的前驅物的包含二環戊二烯基二苯酚結構的活性酯系硬化劑。
作為其他硬化劑,具體而言可列舉:三苯基膦等膦化合物,四苯基溴化鏻等鏻鹽,2-甲基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、1-氰基乙基-2-甲基咪唑等咪唑類,作為咪唑類與偏苯三甲酸、異氰脲酸或硼等的鹽的咪唑鹽類,三甲基氯化銨等四級銨鹽類,二氮雜雙環化合物,二氮雜雙環化合物與苯酚類或苯酚酚醛清漆樹脂類等的鹽類,三氟化硼與胺類或醚化合物等的錯合化合物,芳香族鏻鹽或芳香族碘鎓鹽等。
環氧樹脂組成物中可根據需要而使用硬化促進劑。作為可使用的硬化促進劑的例子,可列舉:2-甲基咪唑、2-乙基咪唑、2-乙基-4-甲基咪唑等咪唑類,4-二甲基胺基吡啶、2-(二甲基胺基甲基)苯酚、1,8-二氮雜-雙環(5,4,0)十一烯-7等三級胺類,三苯基膦、三環己基膦、三苯基膦三苯基硼烷等膦類,辛酸錫等金屬化合物。於使用硬化促進劑的情況下,相對於本發明的環氧樹脂組成物中的環氧樹脂成分100質量份,硬化促進劑的使用量較佳為0.02質量份~5質量份。藉由使用硬化促進劑,可降低硬化溫度、或縮短硬化時間。
環氧樹脂組成物中可使用有機溶劑或反應性稀釋劑來用於調整黏度。
作為有機溶劑,例如可列舉:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等醯胺類,或乙二醇單甲醚、二甲氧基二乙二醇、乙二醇二乙醚、二乙二醇二乙醚、三乙二醇二甲醚等醚類,或丙酮、甲基乙基酮、甲基異丁基酮、環己酮等酮類,或甲醇、乙醇、1-甲氧基-2-丙醇、2-乙基-1-己醇、苄醇、乙二醇、丙二醇、丁基二乙二醇、松油等醇類,或乙酸丁酯、乙酸甲氧基丁酯、甲基賽路蘇乙酸酯、乙基賽路蘇乙酸酯、乙基二乙二醇乙酸酯、丙二醇單甲醚乙酸酯、卡必醇乙酸酯、苄醇乙酸酯等乙酸酯類,或苯甲酸甲酯、苯甲酸乙酯等苯甲酸酯類,或甲基賽路蘇、乙基賽路蘇、丁基賽路蘇等賽路蘇類,或甲基卡必醇、乙基卡必醇、丁基卡必醇等卡必醇類,或苯、甲苯、二甲苯等芳香族烴類,或二甲基亞碸、乙腈、N-甲基吡咯啶酮等,但並不限定於該些。
作為反應性稀釋劑,例如可列舉:烯丙基縮水甘油醚、丁基縮水甘油醚、2-乙基己基縮水甘油醚、苯基縮水甘油醚、甲苯基縮水甘油醚等單官能縮水甘油醚類,或新癸烷酸縮水甘油酯等單官能縮水甘油酯類等,但並不限定於該些。
該些有機溶劑或反應性稀釋劑較佳為於樹脂組成物中以不揮發成分為90質量%以下而單獨使用或使用混合有多種者,其適當的種類或使用量可根據用途而適宜選擇。例如於印刷配線板用途中,較佳為甲基乙基酮、丙酮、1-甲氧基-2-丙醇等沸點為160℃以下的極性溶劑,樹脂組成物中的使用量以不揮發成分計較佳為40質量%~80質量%。另外,於接著膜用途中,例如較佳為使用酮類、乙酸酯類、卡必醇類、芳香族烴類、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等,其使用量以不揮發成分計較佳為30質量%~60質量%。
環氧樹脂組成物亦可在不損及特性的範圍內調配其他熱硬化性樹脂、熱塑性樹脂。例如可列舉:酚樹脂、苯並噁嗪樹脂、雙馬來醯亞胺樹脂、雙馬來醯亞胺三嗪樹脂、丙烯酸樹脂、石油樹脂、茚樹脂、苯並呋喃茚(coumarone indene)樹脂、苯氧基樹脂、聚胺基甲酸酯樹脂、聚酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、聚醯胺醯亞胺樹脂、聚醚醯亞胺樹脂、聚苯醚樹脂、改質聚苯醚樹脂、聚醚碸樹脂、聚碸樹脂、聚醚醚酮樹脂、聚苯硫醚樹脂、聚乙烯縮甲醛(polyvinyl formal)樹脂、聚矽氧烷化合物、含羥基的聚丁二烯等含反應性官能基的伸烷基樹脂類,但並不限定於該些。
為了提高所得的硬化物的阻燃性,環氧樹脂組成物中可使用公知的各種阻燃劑。作為可使用的阻燃劑,例如可列舉鹵素系阻燃劑、磷系阻燃劑、氮系阻燃劑、矽酮系阻燃劑、無機系阻燃劑、有機金屬鹽系阻燃劑等。就對環境的觀點而言,較佳為不含鹵素的阻燃劑,特佳為磷系阻燃劑。該些阻燃劑可單獨使用,亦可併用兩種以上。
磷系阻燃劑可使用無機磷系化合物、有機磷系化合物的任一種。作為無機磷系化合物,例如可列舉紅磷、磷酸一銨、磷酸二銨、磷酸三銨、多磷酸銨等磷酸銨類,磷酸醯胺等無機系含氮磷化合物。作為有機磷系化合物,例如可列舉脂肪族磷酸酯、磷酸酯化合物、例如PX-200(大八化學工業股份有限公司製造)等縮合磷酸酯類、聚磷腈(polyphosphazene)、膦酸化合物、次膦酸化合物、氧化膦化合物、正膦(phosphorane)化合物、有機系含氮磷化合物等通用有機磷系化合物,或次膦酸的金屬鹽,除此以外可列舉9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(2,5-二羥基苯基)-10H-9-氧雜-10-磷雜菲-10-氧化物、10-(2,7-二羥基萘基)-10H-9-氧雜-10-磷雜菲-10-氧化物等環狀有機磷化合物,或作為使該些化合物與環氧樹脂或酚樹脂等化合物反應而得的衍生物的含磷環氧樹脂或含磷硬化劑等。
作為阻燃劑的調配量,可根據磷系阻燃劑的種類、環氧樹脂組成物的成分、所期望的阻燃性的程度而適宜選擇。例如,環氧樹脂組成物中的有機成分(有機溶劑除外)中的磷含量較佳為0.2質量%~4質量%,更佳為0.4質量%~3.5質量%,進而佳為0.6質量%~3質量%。若磷含量少,則有難以確保阻燃性之虞,若過多,則有對耐熱性造成不良影響之虞。另外,於使用磷系阻燃劑的情況下,亦可併用氫氧化鎂等阻燃助劑。
環氧樹脂組成物中可根據需要而使用填充材。具體而言可列舉:熔融二氧化矽、結晶二氧化矽、氧化鋁、氮化矽、氫氧化鋁、水鋁石(boehmite)、氫氧化鎂、滑石、雲母、碳酸鈣、矽酸鈣、氫氧化鈣、碳酸鎂、碳酸鋇、硫酸鋇、氮化硼、碳、碳纖維、玻璃纖維、氧化鋁纖維、二氧化矽氧化鋁纖維、碳化矽纖維、聚酯纖維、纖維素纖維、芳族聚醯胺纖維、陶瓷纖維、微粒子橡膠、矽酮橡膠、熱塑性彈性體、碳黑、顏料等。作為使用填充材的理由,一般可列舉耐衝擊性的提高效果。另外,於使用氫氧化鋁、水鋁石、氫氧化鎂等金屬氫氧化物的情況下,具有作為阻燃助劑起作用而阻燃性提高的效果。相對於環氧樹脂組成物整體,該些填充材的調配量較佳為1質量%~150質量%,更佳為10質量%~70質量%。若調配量多,則有作為積層板用途而所需的接著性降低之虞,進而有硬化物變脆而無法獲得充分的機械物性之虞。另外,若調配量少,則有無法發揮硬化物的耐衝擊性提高等調配填充材的效果之虞。
於將環氧樹脂組成物製成板狀基板等的情況下,就其尺寸穩定性、彎曲強度等方面而言,可列舉纖維狀者作為較佳的填充材。更佳為列舉將玻璃纖維編為網狀的玻璃纖維基板。
環氧樹脂組成物可進一步根據需要而調配矽烷偶合劑、抗氧化劑、脫模劑、消泡劑、乳化劑、觸變性賦予劑、平滑劑、阻燃劑、顏料等各種添加劑。相對於環氧樹脂組成物,該些添加劑的調配量較佳為0.01質量%~20質量%的範圍。
環氧樹脂組成物可藉由含浸於纖維狀基材中而製成印刷配線板等中所使用的預浸體。作為纖維狀基材,可使用玻璃等無機纖維,或聚酯樹脂等、多胺樹脂、聚丙烯酸樹脂、聚醯亞胺樹脂、芳香族聚醯胺樹脂等有機質纖維的織布或不織布,但並不限定於此。作為由環氧樹脂組成物製造預浸體的方法,並無特別限定,例如是於將環氧樹脂組成物浸漬並含浸於利用有機溶劑調整黏度而製成的樹脂清漆中後,進行加熱乾燥而使樹脂成分半硬化(B階段化),獲得預浸體,例如可於100℃~200℃下加熱乾燥1分鐘~40分鐘。此處,預浸體中的樹脂量較佳為樹脂成分為30質量%~80質量%。
另外,為了使預浸體硬化,可使用一般製造印刷配線板時所使用的積層板的硬化方法,但並不限定於此。例如,於使用預浸體形成積層板的情況下,積層一片或多片預浸體,在單側或兩側配置金屬箔而構成積層物,對該積層物進行加熱、加壓而使其積層一體化。此處,作為金屬箔,可單獨使用銅、鋁、黃銅、鎳等,且可使用合金、複合的金屬箔。而且,可藉由對所製成的積層物進行加壓加熱而使預浸體硬化,獲得積層板。此時,較佳的是將加熱溫度設為160℃~220℃,將加壓壓力設為50 N/cm2
~500 N/cm2
,將加熱加壓時間設為40分鐘~240分鐘,從而可獲得目標硬化物。若加熱溫度低,則硬化反應不能充分進行,若加熱溫度高,則有環氧樹脂組成物開始分解之虞。另外,若加壓壓力低,則有在所得的積層板的內部殘留氣泡,電氣特性降低的情況,若加壓壓力高,則有樹脂在硬化前流動,無法獲得所希望厚度的硬化物之虞。進而,若加熱加壓時間短,則有不能充分進行硬化反應之虞,若加熱加壓時間長,則有引起預浸體中的環氧樹脂組成物的熱分解之虞,因而欠佳。
環氧樹脂組成物可藉由利用與公知的環氧樹脂組成物同樣的方法進行硬化而獲得環氧樹脂硬化物。作為用以獲得硬化物的方法,可採用與公知的環氧樹脂組成物同樣的方法,可適宜使用注塑、注入、灌注(potting)、浸漬、滴落塗佈(drip coating)、轉印成形、壓縮成形等或藉由製成樹脂片、帶有樹脂的銅箔、預浸體等形態進行積層並加熱加壓硬化而製成積層板等的方法。此時的硬化溫度通常為100℃~300℃,硬化時間通常為1小時~5小時左右。
本發明的環氧樹脂硬化物可採用積層物、成型物、接著物、塗膜、膜等形態。
製作環氧樹脂組成物,並藉由加熱硬化來評價積層板及硬化物,結果可提供於硬化物中顯現出優異的低介電特性、進而於印刷配線板用途中銅箔剝離強度及層間密接強度優異的環氧硬化性樹脂組成物。
[實施例]
列舉實施例及比較例來對本發明進行具體說明,但本發明並不限定於該些。只要並無特別說明,則「份」表示質量份,「%」表示質量%,「ppm」表示質量ppm。另外,測定方法是分別藉由以下的方法進行測定。
・羥基當量:
依據日本工業標準(Japanese Industrial Standards,JIS)K 0070標準進行測定,單位以「g/eq.」來表示。再者,只要並無特別說明,則酚樹脂的羥基當量是指酚性羥基當量。
・軟化點:
依據JIS K 7234標準、環球法進行測定。具體而言,使用自動軟化點裝置(明達科(Meitec)股份有限公司製造,ASP-MG4)。
・環氧當量:
依據JIS K 7236標準進行測定,單位以「g/eq.」來表示。具體而言,使用自動電位差滴定裝置(平沼產業股份有限公司製造,COM-1600ST),且使用氯仿作為溶劑,加入四乙基溴化銨乙酸溶液,利用0.1 mol/L過氯酸-乙酸溶液進行滴定。
・總氯含量:
依據JIS K 7243-3標準進行測定,單位以「ppm」來表示。具體而言,使用二乙二醇單丁醚作為溶劑,加入1 mol/L氫氧化鉀1,2-丙二醇溶液進行加熱處理後,使用自動電位差滴定裝置(平沼產業股份有限公司製造,COM-1700),利用0.01 mol/L的硝酸銀溶液進行滴定。
・銅箔剝離強度及層間接著力:
依據JIS C 6481進行測定,層間接著力是在第7層與第8層之間進行剝離測定。
・相對介電常數及介電損耗正切:
依據印刷電路協會(Institute of Printed Circuits,IPC)-TM-650 2.5.5.9進行測定。具體而言,利用設定為105℃的烘箱將試樣乾燥2小時,於乾燥器(desiccator)中放冷後,使用安捷倫科技(AGILENT Technologies)公司製造的材料分析儀(material analyzer),藉由電容法求出頻率1 GHz下的相對介電常數及介電損耗正切,藉此進行評價。
・玻璃轉移溫度(Tg):
由依據IPC-TM-650 2.4.25.c,利用差示掃描量熱裝置(日立高科技科學股份有限公司製造,EXSTAR6000 DSC6200)在20℃/分鐘的升溫條件下進行測定時的DSC・Tgm(相對於玻璃狀態與橡膠狀態的切線而言的變異曲線的中間溫度)的溫度來表示。
・GPC(凝膠滲透層析法)測定:
使用在本體(東曹(Tosoh)股份有限公司製造的HLC-8220GPC)中串列地包含管柱(東曹股份有限公司製造的TSKgelG4000HXL、TSKgelG3000HXL、TSKgelG2000HXL)的裝置,管柱溫度設為40℃。另外,溶離液使用四氫呋喃(THF),流速設為1 mL/分鐘,檢測器使用示差折射率檢測器。測定試樣是使用50 μL的將樣品0.1 g溶解於10 mL的THF中並利用微濾器(microfilter)進行過濾而得者。資料處理是使用東曹股份有限公司製造的GPC-8020型號II版本6.00。
・IR:
使用傅立葉轉換型紅外分光光度計(珀金埃爾默精確(Perkin Elmer Precisely)製造,Spectrum One FT-IR Spectrometer 1760X),單元使用KRS-5,將溶解於THF中的樣品塗佈於單元上,使其乾燥後,測定波數650 cm-1
~4000 cm-1
的吸光度。
・ESI-MS:使用質量分析儀(島津製作所製造,LCMS-2020),作為流動相使用乙腈及水,測定溶解於乙腈中的樣品,藉此進行質量分析。
實施例、比較例中使用的簡稱如下。
[環氧樹脂]
E1:實施例6中得到的環氧樹脂
E2:實施例7中得到的環氧樹脂
E3:實施例8中得到的環氧樹脂
E4:實施例9中得到的環氧樹脂
E5:實施例10中得到的環氧樹脂
HE1:合成例7(比較例2)中得到的環氧樹脂
HE2:苯酚-二環戊二烯型環氧樹脂(迪愛生(DIC)股份有限公司製造,HP-7200H,環氧當量280,軟化點83℃)
[硬化劑]
P1:實施例1中得到的酚樹脂
P2:實施例2中得到的酚樹脂
P3:實施例3中得到的酚樹脂
P4:實施例4中得到的酚樹脂
P5:實施例5中得到的酚樹脂
A1:合成例1中得到的酚樹脂
A2:合成例2中得到的酚樹脂
A3:合成例3中得到的酚樹脂
A4:合成例4中得到的酚樹脂
A5:合成例5中得到的酚樹脂
A6:合成例6(比較例1)中得到的芳香族改質酚樹脂
A7:苯酚酚醛清漆樹脂(愛克工業股份有限公司製造,昭能(Shonol)BRG-557,羥基當量105,軟化點80℃)
[硬化促進劑]
C1:2E4MZ:2-乙基-4-甲基咪唑(四國化成工業股份有限公司製造,固唑(Curezol)2E4MZ)
合成例1
向具備攪拌機、溫度計、氮氣吹入管、滴液漏斗及冷卻管的包含玻璃製可分離式燒瓶的反應裝置中裝入鄰甲酚400份、47%BF3
醚錯合物6.6份,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯61.1份(相對於鄰甲酚為0.12倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣10份。進而添加10%的草酸水溶液18份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入1080份的MIBK來溶解生成物,加入80℃的溫水320份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得153份的紅褐色的酚樹脂(A1)。羥基當量為185,軟化點為79℃。GPC中的Mw為440,Mn為400,m=0體含量為0.9面積%,m=1體含量為75.8面積%,m=2體以上的含量為23.3面積%。
合成例2
向與合成例1同樣的反應裝置中裝入間甲酚360份、47%BF3
醚錯合物5.9份,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯55.0份(相對於間甲酚為0.12倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣9份。進而添加10%的草酸水溶液16份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入970份的MIBK來溶解生成物,加入80℃的溫水290份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得136份的紅褐色的酚樹脂(A2)。羥基當量為188,軟化點為100℃。GPC中的Mw為450,Mn為420,m=0體含量為0.5面積%,m=1體含量為76.5面積%,m=2體以上的含量為22.9面積%。
合成例3
向與合成例1同樣的反應裝置中裝入2,6-二甲酚500份、47%BF3
醚錯合物7.3份,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯67.6份(相對於2,6-二甲酚為0.12倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣11份。進而添加10%的草酸水溶液19份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入1320份的MIBK來溶解生成物,加入80℃的溫水400份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得164份的紅褐色的酚樹脂(A3)。羥基當量為195,軟化點為73℃。GPC中的Mw為470,Mn為440,m=0體含量為2.8面積%,m=1體含量為86.2面積%,m=2體以上的含量為11.0面積%。
合成例4
向與合成例1同樣的反應裝置中裝入2,5-二甲酚360份、47%BF3
醚錯合物5.2份,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯48.7份(相對於2,5-二甲酚為0.12倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣8份。進而添加10%的草酸水溶液14份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入950份的MIBK來溶解生成物,加入80℃的溫水290份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得130份的紅褐色的酚樹脂(A4)。羥基當量為206,軟化點為108℃。GPC中的Mw為450,Mn為420,m=0體含量為2.6面積%,m=1體含量為84.6面積%,m=2體以上的含量為12.9面積%。
合成例5
向與合成例1同樣的反應裝置中裝入苯酚400份、47%BF3
醚錯合物7.5份,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯70.2份(相對於苯酚為0.12倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣12份。進而添加10%的草酸水溶液20份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入1100份的MIBK來溶解生成物,加入80℃的溫水330份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得110份的紅褐色的酚樹脂(A5)。羥基當量為177,軟化點為92℃。GPC中的Mw為460,Mn為390,m=0體含量為0面積%,m=1體含量為66.7面積%,m=2體以上的含量為33.3面積%。
合成例6(比較例1)
向與合成例1同樣的反應裝置中裝入105份的苯酚酚醛清漆樹脂(羥基當量105、軟化點130℃)、0.1份的對甲苯磺酸,升溫至150℃。在保持為相同溫度的同時,歷時3小時滴加苯乙烯94份,進而於相同溫度下繼續攪拌1小時。其後,溶解於500份的MIBK中,於80℃下進行5次水洗。繼而,減壓蒸餾除去MIBK,獲得芳香族改質苯酚酚醛清漆樹脂(A6)。羥基當量為199,軟化點為110℃。
實施例1
向與合成例1同樣的反應裝置中裝入合成例1中得到的酚樹脂(A1)121份、47%BF3
醚錯合物1.2份、30份的MIBK,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯36.3份(相對於酚樹脂為0.42倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣2份。進而添加10%的草酸水溶液3份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃。加入340份的MIBK來溶解生成物,加入80℃的溫水110份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得155份的紅褐色的酚樹脂(A6)。羥基當量為259,軟化點為106℃,吸收比(A3040
/A1210
)為0.19。測定由ESI-MS(負)所得的質譜,結果確認到M-
=347、479、587、719。將所獲得的酚樹脂(P1)的GPC示於圖1中,將IR圖示於圖2中。GPC中的Mw為690,Mn為530,n=0體含量為0.7面積%,n=1體含量為52.6面積%,n=2體以上的含量為46.6面積%。
實施例2
向與合成例1同樣的反應裝置中裝入合成例2中得到的酚樹脂(A2)101份、47%BF3
醚錯合物1.0份、25份的MIBK,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯30.2份(相對於酚樹脂為0.42倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣2份。進而添加10%的草酸水溶液3份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃。加入280份的MIBK來溶解生成物,加入80℃的溫水90份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得125份的紅褐色的酚樹脂(P2)。羥基當量為309,軟化點為152℃,吸收比(A3040
/A1210
)為0.20。測定由ESI-MS(負)所得的質譜,結果確認到M-
=347、479、587、719。GPC中的Mw為1240,Mn為710,n=0體含量為1.0面積%,n=1體含量為33.3面積%,n=2體以上的含量為65.7面積%。
實施例3
向與合成例1同樣的反應裝置中裝入合成例3中得到的酚樹脂(A3)352份、47%BF3
醚錯合物3.5份、88份的MIBK,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯105.7份(相對於酚樹脂為0.44倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣6份。進而添加10%的草酸水溶液9份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃。加入980份的MIBK來溶解生成物,加入80℃的溫水320份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得444份的紅褐色的酚樹脂(P3)。羥基當量為275,軟化點為96℃,吸收比(A3040
/A1210
)為0.19。測定由ESI-MS(負)所得的質譜,結果確認到M-
=375、507、629、761。GPC中的Mw為720,Mn為530,n=0體含量為6.9面積%,n=1體含量為64.9面積%,n=2體以上的含量為28.2面積%。
實施例4
向與合成例1同樣的反應裝置中裝入合成例4中得到的酚樹脂(A4)101份、47%BF3
醚錯合物1.0份、25份的MIBK,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯30.2份(相對於酚樹脂為0.44倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣2份。進而添加10%的草酸水溶液3份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃。加入280份的MIBK來溶解生成物,加入80℃的溫水90份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得127份的紅褐色的酚樹脂(P4)。羥基當量為355,軟化點為141℃,吸收比(A3040
/A1210
)為0.20。測定由ESI-MS(負)所得的質譜,結果確認到M-
=375、507、629、761。GPC中的Mw為790,Mn為570,n=0體含量為5.1面積%,n=1體含量為58.8面積%,n=2體以上的含量為36.1面積%。
實施例5
向與合成例1同樣的反應裝置中裝入合成例5中得到的酚樹脂(A5)100份、47%BF3
醚錯合物1.0份、25份的MIBK,一邊攪拌一邊加溫至100℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯30.0份(相對於酚樹脂為0.40倍莫耳)。進而於115℃~125℃的溫度下反應4小時,加入氫氧化鈣2份。進而添加10%的草酸水溶液3份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃。加入280份的MIBK來溶解生成物,加入80℃的溫水90份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得126份的紅褐色的酚樹脂(P5)。羥基當量為287,軟化點為150℃,吸收比(A3040
/A1210
)為0.23。測定由ESI-MS(負)所得的質譜,結果確認到M-
=319、451、545、677。GPC中的Mw為1390,Mn為760,n=0體含量為0.5面積%,n=1體含量為23.0面積%,n=2體以上的含量為76.5面積%。
實施例6
向具備攪拌機、溫度計、氮氣吹入管、滴液漏斗及冷卻管的反應裝置中,加入實施例1中得到的酚樹脂(P1)139份、表氯醇247份及二乙二醇二甲醚74份,加溫至65℃。於125 mmHg的減壓下,一邊保持為63℃~67℃的溫度,一邊用4小時滴加49%氫氧化鈉水溶液48.0份。在此期間,使表氯醇與水共沸,將流出的水依次除去至系統外。反應結束後,於5 mmHg、180℃的條件下回收表氯醇,加入390份的MIBK來溶解生成物。其後,加入120份的水來溶解副生成的食鹽,靜置而將下層的食鹽水分離除去。利用磷酸水溶液中和後,對樹脂溶液進行水洗、過濾,直至水洗液變為中性。於5 mmHg的減壓下,加溫至180℃,蒸餾除去MIBK,獲得159份的紅褐色的二環戊二烯型環氧樹脂(E1)。環氧當量為328,為總氯含量950 ppm、軟化點82℃的樹脂。將所獲得的環氧樹脂(E1)的GPC示於圖3中,將IR圖示於圖4中。GPC中的Mw為780,Mn為560,k=0體含量為1.3面積%,k=1體含量為49.7面積%,k=2體以上的含量為49.0面積%。
實施例7
向與實施例6同樣的反應裝置中加入實施例2中得到的酚樹脂(P2)100份、表氯醇150份及二乙二醇二甲醚45份,加溫至65℃。於125 mmHg的減壓下,一邊保持為63℃~67℃的溫度,一邊用4小時滴加49%氫氧化鈉水溶液29.1份。在此期間,使表氯醇與水共沸,將流出的水依次除去至系統外。反應結束後,於5 mmHg、180℃的條件下回收表氯醇,加入280份的MIBK來溶解生成物。其後,加入80份的水來溶解副生成的食鹽,靜置而將下層的食鹽水分離除去。利用磷酸水溶液中和後,對樹脂溶液進行水洗、過濾,直至水洗液變為中性。於5 mmHg的減壓下,加溫至180℃,蒸餾除去MIBK,獲得109份的紅褐色的二環戊二烯型環氧樹脂(E2)。環氧當量為382,為總氯含量1180 ppm、軟化點130℃的樹脂。GPC中的Mw為1460,Mn為760,k=0體含量為0.7面積%,k=1體含量為31.0面積%,k=2體以上的含量為68.3面積%。
實施例8
向與實施例6同樣的反應裝置中加入實施例3中得到的酚樹脂(P3)370份、表氯醇622份及二乙二醇二甲醚187份,加溫至65℃。於125 mmHg的減壓下,一邊保持為63℃~67℃的溫度,一邊用4小時滴加49%氫氧化鈉水溶液120.7份。在此期間,使表氯醇與水共沸,將流出的水依次除去至系統外。反應結束後,於5 mmHg、180℃的條件下回收表氯醇,加入1040份的MIBK來溶解生成物。其後,加入310份的水來溶解副生成的食鹽,靜置而將下層的食鹽水分離除去。利用磷酸水溶液中和後,對樹脂溶液進行水洗、過濾,直至水洗液變為中性。於5 mmHg的減壓下,加溫至180℃,蒸餾除去MIBK,獲得425份的紅褐色的二環戊二烯型環氧樹脂(E3)。環氧當量為358,為總氯含量520 ppm、軟化點80℃的樹脂。GPC中的Mw為870,Mn為570,k=0體含量為5.5面積%,k=1體含量為61.8面積%,k=2體以上的含量為32.6面積%。
實施例9
向與實施例6同樣的反應裝置中加入實施例4中得到的酚樹脂(P4)101份、表氯醇131份及二乙二醇二甲醚39份,加溫至65℃。於125 mmHg的減壓下,一邊保持為63℃~67℃的溫度,一邊用4小時滴加49%氫氧化鈉水溶液25.5份。在此期間,使表氯醇與水共沸,將流出的水依次除去至系統外。反應結束後,於5 mmHg、180℃的條件下回收表氯醇,加入270份的MIBK來溶解生成物。其後,加入80份的水來溶解副生成的食鹽,靜置而將下層的食鹽水分離除去。利用磷酸水溶液中和後,對樹脂溶液進行水洗、過濾,直至水洗液變為中性。於5 mmHg的減壓下,加溫至180℃,蒸餾除去MIBK,獲得112份的紅褐色的二環戊二烯型環氧樹脂(E4)。環氧當量為429,為總氯含量540 ppm、軟化點125℃的樹脂。GPC中的Mw為1010,Mn為630,k=0體含量為4.3面積%,k=1體含量為49.9面積%,k=2體以上的含量為45.8面積%。
實施例10
向與實施例6同樣的反應裝置中加入實施例5中得到的酚樹脂(P5)102份、表氯醇165份及二乙二醇二甲醚49份,加溫至65℃。於125 mmHg的減壓下,一邊保持為63℃~67℃的溫度,一邊用4小時滴加49%氫氧化鈉水溶液32.0份。在此期間,使表氯醇與水共沸,將流出的水依次除去至系統外。反應結束後,於5 mmHg、180℃的條件下回收表氯醇,加入290份的MIBK來溶解生成物。其後,加入90份的水來溶解副生成的食鹽,靜置而將下層的食鹽水分離除去。利用磷酸水溶液中和後,對樹脂溶液進行水洗、過濾,直至水洗液變為中性。於5 mmHg的減壓下,加溫至180℃,蒸餾除去MIBK,獲得97份的紅褐色的二環戊二烯型環氧樹脂(E5)。環氧當量為382,為總氯含量560 ppm、軟化點132℃的樹脂。GPC中的Mw為2960,Mn為920,k=0體含量為0.6面積%,k=1體含量為19.4面積%,k=2體以上的含量為80.0面積%。
合成例7(比較例2)
向與實施例6同樣的反應裝置中加入合成例3中得到的酚樹脂(A3)150份、表氯醇356份及二乙二醇二甲醚107份,加溫至65℃。於125 mmHg的減壓下,一邊保持為63℃~67℃的溫度,一邊用4小時滴加49%氫氧化鈉水溶液69.1份。在此期間,使表氯醇與水共沸,將流出的水依次除去至系統外。反應結束後,於5 mmHg、180℃的條件下回收表氯醇,加入450份的MIBK來溶解生成物。其後,加入140份的水來溶解副生成的食鹽,靜置而將下層的食鹽水分離除去。利用磷酸水溶液中和後,對樹脂溶液進行水洗、過濾,直至水洗液變為中性。於5 mmHg的減壓下,加溫至180℃,蒸餾除去MIBK,獲得183份的紅褐色的二環戊二烯型環氧樹脂(HE1)。環氧當量為261,為總氯含量710 ppm、軟化點55℃的樹脂。GPC中的Mw為670,Mn為570,k=0體含量為2.3面積%,k=1體含量為73.1面積%,k=2體以上的含量為24.6面積%。
實施例11
調配100份的環氧樹脂(E1)作為環氧樹脂、32份的酚樹脂(A7)作為硬化劑、0.20份的C1作為硬化促進劑,溶解於利用甲基乙基酮(Methyl Ethyl Ketone,MEK)、丙二醇單甲醚、N,N-二甲基甲醯胺進行了調整的混合溶劑中,獲得環氧樹脂組成物清漆。將所獲得的環氧樹脂組成物清漆含浸於玻璃布(日東紡績股份有限公司製造,WEA 7628 XS13,厚度0.18 mm)中。將已進行含浸的玻璃布於150℃的熱風循環烘箱中乾燥9分鐘,獲得預浸體。將所獲得的預浸體8片與銅箔(三井金屬礦業股份有限公司製造,3EC-III,厚度35 μm)上下重疊,於130℃×15分鐘+190℃×80分鐘的溫度條件下進行2 MPa的真空壓製,獲得厚度1.6 mm的積層板。將積層板的銅箔剝離強度及層間接著力的結果示於表1中。
另外,將所獲得的預浸體拆開,製成通過100目的篩的粉狀的預浸體粉末。將所獲得的預浸體粉末放入氟樹脂製的模具中,於130℃×15分鐘+190℃×80分鐘的溫度條件下進行2 MPa的真空壓製,獲得50 mm見方×2 mm厚的試驗片。將試驗片的相對介電常數及介電損耗正切的結果示於表1中。
實施例12~實施例36及比較例11~比較例20
以表1~表4的調配量(份)調配,進行與實施例11同樣的操作,獲得積層板及試驗片。硬化促進劑的使用量設為可將清漆凝膠時間調整為300秒左右的量。進行與實施例11同樣的試驗,將其結果示於表1~表4中。
[表1]
實施例11 | 實施例12 | 實施例13 | 實施例14 | 實施例15 | 比較例11 | 比較例12 | |
E1 | 100 | ||||||
E2 | 100 | ||||||
E3 | 100 | ||||||
E4 | 100 | ||||||
E5 | 100 | ||||||
HE1 | 100 | ||||||
HE2 | 100 | ||||||
A7 | 32 | 32 | 29 | 29 | 29 | 40 | 38 |
C1 | 0.20 | 0.15 | 0.30 | 0.25 | 0.15 | 0.20 | 0.10 |
銅箔剝離強度 (kN/m) | 1.3 | 1.3 | 1.4 | 1.3 | 1.3 | 1.7 | 1.6 |
層間接著力 (kN/m) | 1.1 | 1.1 | 1.2 | 1.2 | 1.1 | 1.4 | 1.2 |
相對介電常數 | 2.89 | 2.93 | 2.90 | 2.91 | 2.95 | 3.01 | 3.17 |
介電損耗正切 | 0.014 | 0.014 | 0.013 | 0.013 | 0.016 | 0.015 | 0.021 |
Tg(℃) | 171 | 172 | 168 | 169 | 175 | 174 | 184 |
[表2]
實施例16 | 實施例17 | 實施例18 | 實施例19 | 實施例20 | 比較例13 | 比較例14 | |
E3 | 100 | 100 | 100 | ||||
HE2 | 100 | 100 | 100 | 100 | |||
P3 | 38 | 38 | 38 | 98 | 49 | ||
A3 | 27 | 70 | |||||
A5 | 25 | 63 | |||||
A7 | 15 | 19 | |||||
C1 | 0.40 | 0.38 | 0.36 | 0.25 | 0.20 | 0.22 | 0.17 |
銅箔剝離強度 (kN/m) | 1.4 | 1.3 | 1.3 | 1.4 | 1.4 | 1.7 | 1.6 |
層間接著力 (kN/m) | 1.3 | 1.1 | 1.1 | 1.1 | 1.1 | 1.4 | 1.2 |
相對介電常數 | 2.71 | 2.75 | 2.78 | 2.89 | 2.90 | 3.03 | 3.07 |
介電損耗正切 | 0.009 | 0.010 | 0.011 | 0.013 | 0.013 | 0.016 | 0.020 |
Tg(℃) | 156 | 158 | 165 | 175 | 171 | 158 | 168 |
[表3]
實施例21 | 實施例22 | 實施例23 | 實施例24 | 實施例25 | 比較例15 | 比較例16 | 比較例17 | 比較例18 | 比較例19 | 比較例20 | |
HE1 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
P1 | 99 | ||||||||||
P2 | 119 | ||||||||||
P3 | 106 | ||||||||||
P4 | 136 | ||||||||||
P5 | 110 | ||||||||||
A1 | 71 | ||||||||||
A2 | 71 | ||||||||||
A3 | 75 | ||||||||||
A4 | 75 | ||||||||||
A5 | 68 | ||||||||||
A6 | 76 | ||||||||||
C1 | 0.38 | 0.38 | 0.42 | 0.42 | 0.28 | 0.35 | 0.35 | 0.40 | 0.40 | 0.30 | 0.52 |
銅箔剝離強度 (kN/m) | 1.3 | 1.3 | 1.5 | 1.5 | 1.4 | 1.6 | 1.6 | 1.8 | 1.8 | 1.7 | 1.6 |
層間接著力 (kN/m) | 1.1 | 1.1 | 1.3 | 1.1 | 1.2 | 1.4 | 1.4 | 1.6 | 1.5 | 1.4 | 0.8 |
相對介電常數 | 2.85 | 2.89 | 2.80 | 2.83 | 2.86 | 2.94 | 2.97 | 2.88 | 2.93 | 2.93 | 2.93 |
介電損耗正切 | 0.012 | 0.013 | 0.011 | 0.012 | 0.013 | 0.013 | 0.014 | 0.012 | 0.014 | 0.015 | 0.012 |
Tg(℃) | 164 | 165 | 162 | 165 | 167 | 152 | 154 | 149 | 152 | 157 | 161 |
[表4]
實施例26 | 實施例27 | 實施例28 | 實施例29 | 實施例30 | 實施例31 | 實施例32 | 實施例33 | 實施例34 | 實施例35 | 實施例36 | |
E3 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
P1 | 72 | ||||||||||
P2 | 73 | ||||||||||
P3 | 77 | ||||||||||
P4 | 76 | ||||||||||
P5 | 80 | ||||||||||
A1 | 52 | ||||||||||
A2 | 52 | ||||||||||
A3 | 54 | ||||||||||
A4 | 54 | ||||||||||
A5 | 49 | ||||||||||
A6 | 56 | ||||||||||
C1 | 0.38 | 0.38 | 0.40 | 0.40 | 0.30 | 0.35 | 0.35 | 0.38 | 0.38 | 0.34 | 0.60 |
銅箔剝離強度 (kN/m) | 1.1 | 1.1 | 1.2 | 1.2 | 1.0 | 1.4 | 1.4 | 1.5 | 1.5 | 1.4 | 1.2 |
層間接著力 (kN/m) | 1.0 | 1.0 | 1.1 | 1.0 | 0.9 | 1.3 | 1.3 | 1.4 | 1.4 | 1.2 | 0.7 |
相對介電常數 | 2.71 | 2.74 | 2.65 | 2.68 | 2.80 | 2.80 | 2.83 | 2.75 | 2.78 | 2.81 | 2.81 |
介電損耗正切 | 0.009 | 0.010 | 0.008 | 0.009 | 0.011 | 0.010 | 0.011 | 0.009 | 0.010 | 0.012 | 0.011 |
Tg(℃) | 162 | 163 | 160 | 162 | 165 | 151 | 153 | 148 | 150 | 155 | 163 |
如由該些結果可知般,實施例中得到的含有二環戊烯基的二環戊二烯型環氧樹脂、含有二環戊烯基的二環戊二烯型酚樹脂、以及含有該些的樹脂組成物能夠提供顯現出非常良好的低介電特性、進而接著力亦優異的樹脂硬化物。
本發明的酚樹脂可於塗料、土木接著、注塑、電氣電子材料、膜材料等多方面中使用,尤其是於印刷配線基板用途中有用。
無
圖1是實施例1中得到的酚樹脂的凝膠滲透層析(gel permeation chromatography,GPC)圖。
圖2是實施例1中得到的酚樹脂的紅外(Infrared,IR)圖。
圖3是實施例6中得到的環氧樹脂的GPC圖。
圖4是實施例6中得到的環氧樹脂的IR圖。
Claims (13)
- 如請求項1所述的酚樹脂,其中R1 為甲基或苯基,i為1或2。
- 如請求項3所述的酚樹脂的製造方法,其中相對於二環戊二烯100質量份,使用0.001質量份~20質量份的路易斯酸。
- 一種環氧樹脂的製造方法,其是如請求項5所述的環氧樹脂的製造方法,其特徵在於,相對於如請求項1所述的酚樹脂的酚性羥基1莫耳,使1莫耳~20莫耳的表鹵醇於鹼金屬氫氧化物的存在下進行反應。
- 一種環氧樹脂組成物,其是含有環氧樹脂及硬化劑的環氧樹脂組成物,其特徵在於,硬化劑的一部分或全部為如請求項1所述的酚樹脂。
- 一種環氧樹脂組成物,其是含有環氧樹脂及硬化劑的環氧樹脂組成物,其特徵在於,環氧樹脂的一部分或全部為如請求項5所述的環氧樹脂。
- 一種環氧樹脂組成物,其是含有環氧樹脂及硬化劑的環氧樹脂組成物,其特徵在於,硬化劑的一部分或全部為如請求項1所述的酚樹脂,且環氧樹脂的一部分或全部為如請求項5所述的環氧樹脂。
- 一種預浸體,其特徵在於,使用如請求項7至請求項9中任一項所述的環氧樹脂組成物。
- 一種積層板,其特徵在於,使用如請求項7至請求項9中任一項所述的環氧樹脂組成物。
- 一種印刷配線基板,其特徵在於,使用如請求項7至請求項9中任一項所述的環氧樹脂組成物。
- 一種硬化物,其是將如請求項7至請求項9中任一項所述的環氧樹脂組成物硬化而成。
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JP3820834B2 (ja) | 2000-02-28 | 2006-09-13 | 大日本インキ化学工業株式会社 | 格子状通電端子配設半導体装置に用いられる回路基板用樹脂組成物、格子状通電端子配設半導体装置用回路基板及び格子状通電端子配設半導体装置 |
JP5337735B2 (ja) * | 2010-02-16 | 2013-11-06 | ナン ヤ プラスティクス コーポレーション | 積層板用の新規臭素化エポキシ樹脂及びその製造方法 |
US8039560B1 (en) * | 2010-04-01 | 2011-10-18 | Nan Ya Plastics Corporation | Low dielectric brominated resin with a symmetric or saturated heterocyclic alphatic molecular structure and the preparation thereof |
WO2020129724A1 (ja) * | 2018-12-19 | 2020-06-25 | 日鉄ケミカル&マテリアル株式会社 | フェノール樹脂、エポキシ樹脂、エポキシ樹脂組成物およびその硬化物 |
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2021
- 2021-06-04 JP JP2022530532A patent/JPWO2021251289A1/ja active Pending
- 2021-06-04 CN CN202180039891.XA patent/CN115916863A/zh active Pending
- 2021-06-04 US US18/008,666 patent/US20230272155A1/en active Pending
- 2021-06-04 KR KR1020227040202A patent/KR20230008113A/ko not_active Application Discontinuation
- 2021-06-04 WO PCT/JP2021/021361 patent/WO2021251289A1/ja active Application Filing
- 2021-06-09 TW TW110120916A patent/TW202200662A/zh unknown
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KR20230008113A (ko) | 2023-01-13 |
US20230272155A1 (en) | 2023-08-31 |
WO2021251289A1 (ja) | 2021-12-16 |
CN115916863A (zh) | 2023-04-04 |
JPWO2021251289A1 (zh) | 2021-12-16 |
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