JP2005307031A - エポキシ樹脂組成物及びその硬化物 - Google Patents
エポキシ樹脂組成物及びその硬化物 Download PDFInfo
- Publication number
- JP2005307031A JP2005307031A JP2004126686A JP2004126686A JP2005307031A JP 2005307031 A JP2005307031 A JP 2005307031A JP 2004126686 A JP2004126686 A JP 2004126686A JP 2004126686 A JP2004126686 A JP 2004126686A JP 2005307031 A JP2005307031 A JP 2005307031A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- resin composition
- cured product
- epoxy
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 172
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 172
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 40
- 239000011342 resin composition Substances 0.000 claims abstract description 30
- 239000004065 semiconductor Substances 0.000 claims abstract description 29
- 125000003700 epoxy group Chemical class 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 19
- -1 phenol compound Chemical class 0.000 claims description 16
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 239000011229 interlayer Substances 0.000 claims description 7
- 239000011889 copper foil Substances 0.000 claims description 5
- 239000011810 insulating material Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 abstract description 33
- 239000011347 resin Substances 0.000 abstract description 33
- 239000003566 sealing material Substances 0.000 abstract description 7
- 238000001723 curing Methods 0.000 description 43
- 239000000047 product Substances 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 37
- 238000000034 method Methods 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 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 description 20
- 229920003986 novolac Polymers 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000005011 phenolic resin Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 150000002989 phenols Chemical class 0.000 description 14
- 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 13
- 238000010438 heat treatment Methods 0.000 description 13
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 230000003014 reinforcing effect Effects 0.000 description 5
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000004760 aramid Substances 0.000 description 4
- 229920003235 aromatic polyamide Polymers 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000008393 encapsulating agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 3
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 2
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 2
- KGSFMPRFQVLGTJ-UHFFFAOYSA-N 1,1,2-triphenylethylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 KGSFMPRFQVLGTJ-UHFFFAOYSA-N 0.000 description 2
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- UWLINSANVPZJBA-UHFFFAOYSA-N 2-(chloromethyl)oxirane hydrate Chemical compound O.ClCC1CO1 UWLINSANVPZJBA-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- MPWGZBWDLMDIHO-UHFFFAOYSA-N 3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1 MPWGZBWDLMDIHO-UHFFFAOYSA-N 0.000 description 2
- UFERIGCCDYCZLN-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-1h-indene Chemical compound C1C=CCC2CC=CC21 UFERIGCCDYCZLN-UHFFFAOYSA-N 0.000 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 description 2
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229930006722 beta-pinene Natural products 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012796 inorganic flame retardant Chemical class 0.000 description 2
- 239000012774 insulation material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 229940087305 limonene Drugs 0.000 description 2
- 235000001510 limonene Nutrition 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000007788 roughening Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GDYAUGXOIOIFLD-UHFFFAOYSA-N 1-methylnaphthalene-2,3-diol Chemical compound C1=CC=C2C(C)=C(O)C(O)=CC2=C1 GDYAUGXOIOIFLD-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- CZAZXHQSSWRBHT-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-3,4,5,6-tetramethylphenol Chemical compound OC1=C(C)C(C)=C(C)C(C)=C1C1=CC=CC=C1O CZAZXHQSSWRBHT-UHFFFAOYSA-N 0.000 description 1
- QRKCWASFYYFORH-UHFFFAOYSA-N 2-(6-hydroxy-2,3,4-trimethylphenyl)-3,4,5-trimethylphenol Chemical compound CC1=C(C)C(C)=CC(O)=C1C1=C(C)C(C)=C(C)C=C1O QRKCWASFYYFORH-UHFFFAOYSA-N 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- ZUTYZAFDFLLILI-UHFFFAOYSA-N 4-sec-Butylphenol Chemical compound CCC(C)C1=CC=C(O)C=C1 ZUTYZAFDFLLILI-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XYHUIOCRXXWEAX-UHFFFAOYSA-N cyclopenta-1,3-diene;phenol Chemical compound C1C=CC=C1.OC1=CC=CC=C1 XYHUIOCRXXWEAX-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000009503 electrostatic coating Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 1
- NCAVLSOYLINKKP-UHFFFAOYSA-N naphthalene-1,4-diol;naphthalene-1,5-diol Chemical compound C1=CC=C2C(O)=CC=CC2=C1O.C1=CC=C2C(O)=CC=C(O)C2=C1 NCAVLSOYLINKKP-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010125 resin casting Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- VLCLHFYFMCKBRP-UHFFFAOYSA-N tricalcium;diborate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]B([O-])[O-].[O-]B([O-])[O-] VLCLHFYFMCKBRP-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Abstract
【解決手段】 β−メチル基置換型エポキシ基を有するエポキシ樹脂(A)と硬化剤(B)とを含有し、得られる硬化物の周波数1GHzでの誘電率が3.0以下であることを特徴とするエポキシ樹脂組成物及びその硬化物。
【選択図】 なし
Description
本発明で用いるβ−メチル基置換型エポキシ基を有するエポキシ樹脂(A)は、下記構造式(1)
(1)ガラス転移温度(Tg)の測定
ティー・エイ・インスツルメント株式会社製粘弾性スペクトロメータ「RSA II」を用いて、周波数1Hz、昇温速度3℃/分で測定したtanδのピーク値の温度をガラス転移温度とした。
(2)吸湿率
東京理化株式会社製恒温恒湿装置「KCL−2000A」を用いて、85℃/85%RHの条件下、硬化物試験片を300時間処理した前後の重量変化率(wt%)を吸湿率として測定した。(試験片のサイズ75×25×2mm)
(3)線膨張係数
セイコー電子工業株式会社製熱機械分析装置「TMA/SS6100」を用いて、昇温速度3℃/分により測定し、40〜60℃まで変化させた際の線膨張係数(α1:ガラス状領域での線膨張係数)を測定した。
(4)誘電特性の測定
JIS−C−6481に準拠した方法により、アジレント・テクノロジー株式会社製インピーダンス・マテリアル・アナライザ「HP4291B」により、絶乾後、23℃、湿度50%の室内に24時間保管した後の硬化物の100MHz、1GHzの周波数における誘電率と誘電正接を測定した。(試験片のサイズ75×25×2mm)
攪拌機、温度計、コンデンサーが装着された2リットルの4つ口フラスコにフェノール338g(3.6モル)を、BF3・フェノール錯体17gを添加し充分混合した。その後ジシクロペンタジエン158g(1.2モル)を、系内温度を110〜120℃に保ちながら4時間要して添加した。その後、系内温度を120℃に保ち、3時間加熱攪拌し、得られた反応生成物溶液にマグネシウム化合物「KW−1000」(商品名;協和化学工業株式会社製)52gを添加し、1時間攪拌して触媒を失活させた後、反応溶液を濾過した。得られた透明溶液から、未反応フェノールを蒸留回収しながら230℃に昇温し、減圧下で4時間ホールドし、固形樹脂343gを得た。このジシクロペンタジエン−フェノール樹脂(I)の水酸基当量は187g/eq、軟化点は125℃であった。
合成例1において、フェノールを338g(3.6モル)から508g(5.4モル)に変更した以外は、合成例1と同様にして固形樹脂325gを得た。このジシクロペンタジエン−フェノール樹脂(II)の水酸基当量は178g/eq、軟化点は112℃であった。
合成例1において、フェノールを338g(3.6モル)から508g(5.4モル)に変更し、更にジシクロペンタジエン158g(1.2モル)をトリシクロペンタジエン238g(1.2モル)に変更した以外は合成例1と同様にして、固形樹脂404gを得た。このトリシクロペンタジエン−フェノール樹脂の水酸基当量は222g/eq、軟化点は129℃であった。
攪拌機、温度計、ディーンスタークトラップ、コンデンサーが装着された2リットルの4つ口フラスコに、合成例1で得られたジシクロペンタジエン−フェノール樹脂(I)300g、β−メチルエピクロルヒドリン852g(8モル)及びジメチルスルホキシド(DMSO)250gを加え溶解した。それを55℃に加熱し、減圧下で49%水酸化ナトリウム(NaOH)水溶液164gを8時間要して滴下した。その際共沸して留出した液体をディーンスタークトラップで水とβ−メチルエピクロルヒドリンに分離し、β−メチルエピクロルヒドリンのみを反応系内に戻しながら反応を行った。滴下後さらに1時間その温度で攪拌した後、120℃まで加熱し、未反応のβ−メチルエピクロルヒドリンを蒸留回収した。次いで得られた粗樹脂溶液にメチルイソブチルケトン(MIBK)600g、水200gを加えて、無機塩及びDMSOを水洗にて除去した。さらに同量の水を用い、5回洗浄し、DMSOを除去した。この溶液に5%NaOH水溶液100gを添加し、85℃で3時間攪拌した。その後静置分液して、下層を除去し、さらに水洗を2回繰り返した。次いで共沸脱水、濾過を経て、MIBKを150℃で脱溶剤して目的のエポキシ樹脂(A−I)400gを得た。このエポキシ樹脂のエポキシ当量は316g/eq、軟化点101℃であった。
合成例2で得られたジシクロペンタジエン−フェノール樹脂(II)300gを使用して、合成例4と同様にして目的のエポキシ樹脂(A−II)438gを得た。このエポキシ樹脂のエポキシ当量は295g/eq、軟化点は89℃であった。
合成例3で得られたトリシクロペンタジエン−フェノール樹脂300gを使用して、合成例4と同様にして目的のエポキシ樹脂(A−III)382gを得た。このエポキシ樹脂のエポキシ当量は352g/eq、軟化点は103℃であった。
合成例1で得られたジシクロペンタジエン−フェノール樹脂(I)300gを使用して、β-メチルエピクロルヒドリン852g(8モル)をエピクロルヒドリン740g(8モル)に変更する以外は、合成例4と同様にして比較用エポキシ樹脂(A’−I)378gを得た(β−メチル基を有しないエポキシ基を有するジシクロペンタジエン−フェノール変性型エポキシ樹脂)。このエポキシ樹脂のエポキシ当量は280g/eq、軟化点91℃であった。
合成例3で得られたトリシクロペンタジエン−フェノール樹脂300gを使用して、β-メチルエピクロルヒドリン852g(8モル)をエピクロルヒドリン740g(8モル)に変更する以外は、合成例4と同様にして比較用エポキシ樹脂(A’−II)382gを得た(β−メチル基を有しないエポキシ基を有するトリシクロペンタジエン−フェノール変性型エポキシ樹脂)。このエポキシ樹脂のエポキシ当量は330g/eq、軟化点は99℃であった。
攪拌機、温度計、冷却器付きデカンターを付した4つ口フラスコにビスフェノールA228g(1モル)にβ−メチルエピクロルヒドリン1065g(10モル)を入れ溶解した。それに減圧下、80℃で48%NaOH水溶液147g(1.8モル)を3時間かけて攪拌しながら滴下した。その間、フラスコを加熱してβ−メチルエピクロルヒドリンと水を蒸留し、デカンターで冷却器で凝縮したβ−メチルエピクロルヒドリンと水とを分離し、β−メチルエピクロルヒドリンをフラスコ内に戻し続けた。さらに30分間攪拌を続けてその後、水180gを加え静置した。下層の食塩水を棄却し、β−メチルエピクロルヒドリンを150℃で蒸留回収した後、粗樹脂にMIBK400gを加え、さらに3%NaOH水溶液200gを加え80℃にて1時間攪拌した。そして下層の水層を棄却した。その後、さらにMIBK層を水200gで水洗し、水を棄却した後、脱水、濾過を経てMIBKを150℃で脱溶剤してエポキシ樹脂(A’−III)352gを得た。このエポキシ樹脂は常温で液状を有し、エポキシ当量は210g/eq、150℃での溶融粘度0.08dPa・sであった。
合成例9において、ビスフェノールAの代わりに1,6−ジヒドロキシナフタレン160gを使用する以外は合成例9と同様にして、エポキシ樹脂(A’−IV)299gを得た。このエポキシ樹脂は常温で半固形を有し、エポキシ当量は176g/eq、150℃での溶融粘度0.12dPa・sであった。
合成例1〜3で得られたフェノール樹脂、及びPHENOLITE TD−2131(フェノール樹脂、大日本インキ化学工業株式会社製、 水酸基当量104g/eq 軟化点80℃)を硬化剤として用い、合成例4〜10で得られたエポキシ樹脂、及びEPICLON N−665−EXP(クレゾールノボラック型エポキシ樹脂、大日本インキ化学工業株式会社製、エポキシ当量203g/eq、150℃での溶融粘度3.2dPa・s)を用い、硬化促進剤として2−エチル−4−メチルイミダゾールを用いて、表1〜2中の配合比に従って調製し、エポキシ樹脂組成物を得た。次いで150℃×20分間の条件でプレス成形し、その後175℃×5時間の条件で後硬化(アフターキュア)して、硬化物を得た。得られた硬化物を各評価に必要な試験片サイズに切り出し、ガラス転移温度(DMA)、吸湿率、線膨張係数(TMA)、誘電率、誘電正接を測定した。それらの結果を表1〜2中に記す。
Claims (14)
- β−メチル基置換型エポキシ基を有するエポキシ樹脂(A)と硬化剤(B)とを含有し、得られる硬化物の周波数1GHzでの誘電率が3.0以下であることを特徴とするエポキシ樹脂組成物。
- エポキシ樹脂(A)のエポキシ当量が230〜400g/eq.である請求項1記載のエポキシ樹脂組成物。
- エポキシ樹脂(A)が脂肪族環状骨格(x)を含有する請求項2記載のエポキシ樹脂組成物。
- 脂肪族環状骨格(x)がジシクロペンタジエン残基及び/又はトリシクロペンタジエン残基である請求項3記載のエポキシ樹脂組成物。
- 硬化剤(B)がフェノール系化合物(b)である請求項1〜4の何れか1項記載のエポキシ樹脂組成物。
- フェノール系化合物(b)の水酸基当量が150〜350g/eq.である請求項5記載のエポキシ樹脂組成物。
- 硬化剤(B)が脂肪族環状骨格(y)を含有する請求項6記載のエポキシ樹脂組成物。
- 脂肪族環状骨格(y)がジシクロペンタジエン残基及び/又はトリシクロペンタジエン残基である請求項7記載のエポキシ樹脂組成物。
- フィルム形状に加工された請求項1〜8の何れか1項記載のエポキシ樹脂組成物。
- 銅箔に塗布された請求項1〜8の何れか1項記載のエポキシ樹脂組成物。
- ビルドアップ層間絶縁材料用である請求項1〜8の何れか1項記載のエポキシ樹脂組成物。
- 請求項1〜11の何れか1項記載のエポキシ樹脂組成物を硬化させて得られることを特徴とする硬化物。
- 周波数1GHzでの誘電正接が0.01以下である請求項11記載の硬化物。
- 半導体パッケージ用サブストレート基板である請求項13記載の硬化物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004126686A JP4716082B2 (ja) | 2004-04-22 | 2004-04-22 | エポキシ樹脂組成物及びその硬化物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004126686A JP4716082B2 (ja) | 2004-04-22 | 2004-04-22 | エポキシ樹脂組成物及びその硬化物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005307031A true JP2005307031A (ja) | 2005-11-04 |
JP4716082B2 JP4716082B2 (ja) | 2011-07-06 |
Family
ID=35436161
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004126686A Expired - Lifetime JP4716082B2 (ja) | 2004-04-22 | 2004-04-22 | エポキシ樹脂組成物及びその硬化物 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4716082B2 (ja) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008156493A (ja) * | 2006-12-25 | 2008-07-10 | Sumitomo Bakelite Co Ltd | 樹脂組成物、プリプレグおよび積層板 |
JP2011140555A (ja) * | 2010-01-07 | 2011-07-21 | Adeka Corp | 硬化性樹脂組成物 |
JP2011157433A (ja) * | 2010-01-29 | 2011-08-18 | Dic Corp | リン原子含有フェノール類の製造方法、リン原子含有フェノール類、硬化性樹脂組成物、その硬化物、プリント配線基板用樹脂組成物、プリント配線基板、フレキシブル配線基板用樹脂組成物、半導体封止材料用樹脂組成物、及びビルドアップ基板用層間絶縁材料用樹脂組成物 |
WO2012141027A1 (ja) * | 2011-04-14 | 2012-10-18 | ソニーケミカル&インフォメーションデバイス株式会社 | 異方性導電フィルム |
JP2014019868A (ja) * | 2012-07-12 | 2014-02-03 | Samsung Electro-Mechanics Co Ltd | ビルドアップ絶縁フィルム用エポキシ樹脂組成物、これから製造された絶縁フィルム、及びこれを備えた多層プリント基板 |
JP2014031465A (ja) * | 2012-08-06 | 2014-02-20 | Dexerials Corp | 回路接続材料 |
JP2021187945A (ja) * | 2020-05-29 | 2021-12-13 | Jfeケミカル株式会社 | 樹脂組成物および硬化物 |
WO2023006005A1 (zh) * | 2021-07-28 | 2023-02-02 | 华为技术有限公司 | 环氧树脂及其制备方法、树脂组合物 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6147725A (ja) * | 1984-08-16 | 1986-03-08 | Yuka Shell Epoxy Kk | 半導体封止用エポキシ樹脂組成物 |
JPH08283379A (ja) * | 1995-04-17 | 1996-10-29 | Dainippon Ink & Chem Inc | 半導体封止材料 |
JPH09151303A (ja) * | 1995-09-25 | 1997-06-10 | Nissan Chem Ind Ltd | エポキシ樹脂組成物 |
JPH10182789A (ja) * | 1996-12-24 | 1998-07-07 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物及び半導体封止材料 |
JP2003082063A (ja) * | 2001-09-12 | 2003-03-19 | Dainippon Ink & Chem Inc | 電子材料用エポキシ樹脂組成物および低誘電性電子材料 |
JP2003252958A (ja) * | 2002-02-28 | 2003-09-10 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物およびその硬化物 |
WO2003087230A1 (fr) * | 2002-04-16 | 2003-10-23 | Hitachi Chemical Co., Ltd. | Composition de resine thermodurcissable, preimpregne et feuille stratifiee utilisant cette composition. |
JP2004026980A (ja) * | 2002-06-25 | 2004-01-29 | Taiyo Ink Mfg Ltd | 熱硬化性樹脂組成物及びそれを用いて作製したプリント配線板 |
JP2004107385A (ja) * | 2002-09-13 | 2004-04-08 | Nippon Steel Chem Co Ltd | インデン含有共重合体、その製造方法及び樹脂組成物 |
-
2004
- 2004-04-22 JP JP2004126686A patent/JP4716082B2/ja not_active Expired - Lifetime
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6147725A (ja) * | 1984-08-16 | 1986-03-08 | Yuka Shell Epoxy Kk | 半導体封止用エポキシ樹脂組成物 |
JPH08283379A (ja) * | 1995-04-17 | 1996-10-29 | Dainippon Ink & Chem Inc | 半導体封止材料 |
JPH09151303A (ja) * | 1995-09-25 | 1997-06-10 | Nissan Chem Ind Ltd | エポキシ樹脂組成物 |
JPH10182789A (ja) * | 1996-12-24 | 1998-07-07 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物及び半導体封止材料 |
JP2003082063A (ja) * | 2001-09-12 | 2003-03-19 | Dainippon Ink & Chem Inc | 電子材料用エポキシ樹脂組成物および低誘電性電子材料 |
JP2003252958A (ja) * | 2002-02-28 | 2003-09-10 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物およびその硬化物 |
WO2003087230A1 (fr) * | 2002-04-16 | 2003-10-23 | Hitachi Chemical Co., Ltd. | Composition de resine thermodurcissable, preimpregne et feuille stratifiee utilisant cette composition. |
JP2004026980A (ja) * | 2002-06-25 | 2004-01-29 | Taiyo Ink Mfg Ltd | 熱硬化性樹脂組成物及びそれを用いて作製したプリント配線板 |
JP2004107385A (ja) * | 2002-09-13 | 2004-04-08 | Nippon Steel Chem Co Ltd | インデン含有共重合体、その製造方法及び樹脂組成物 |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008156493A (ja) * | 2006-12-25 | 2008-07-10 | Sumitomo Bakelite Co Ltd | 樹脂組成物、プリプレグおよび積層板 |
JP2011140555A (ja) * | 2010-01-07 | 2011-07-21 | Adeka Corp | 硬化性樹脂組成物 |
JP2011157433A (ja) * | 2010-01-29 | 2011-08-18 | Dic Corp | リン原子含有フェノール類の製造方法、リン原子含有フェノール類、硬化性樹脂組成物、その硬化物、プリント配線基板用樹脂組成物、プリント配線基板、フレキシブル配線基板用樹脂組成物、半導体封止材料用樹脂組成物、及びビルドアップ基板用層間絶縁材料用樹脂組成物 |
WO2012141027A1 (ja) * | 2011-04-14 | 2012-10-18 | ソニーケミカル&インフォメーションデバイス株式会社 | 異方性導電フィルム |
JP2012219262A (ja) * | 2011-04-14 | 2012-11-12 | Sony Chemical & Information Device Corp | 異方性導電フィルム |
CN103459453A (zh) * | 2011-04-14 | 2013-12-18 | 迪睿合电子材料有限公司 | 各向异性导电膜 |
JP2014019868A (ja) * | 2012-07-12 | 2014-02-03 | Samsung Electro-Mechanics Co Ltd | ビルドアップ絶縁フィルム用エポキシ樹脂組成物、これから製造された絶縁フィルム、及びこれを備えた多層プリント基板 |
JP2014031465A (ja) * | 2012-08-06 | 2014-02-20 | Dexerials Corp | 回路接続材料 |
JP2021187945A (ja) * | 2020-05-29 | 2021-12-13 | Jfeケミカル株式会社 | 樹脂組成物および硬化物 |
WO2023006005A1 (zh) * | 2021-07-28 | 2023-02-02 | 华为技术有限公司 | 环氧树脂及其制备方法、树脂组合物 |
Also Published As
Publication number | Publication date |
---|---|
JP4716082B2 (ja) | 2011-07-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102362604B1 (ko) | 전자 재료용 에폭시 수지 조성물, 그의 경화물 및 전자 부재 | |
KR101715207B1 (ko) | 에폭시 수지 조성물, 경화물, 방열 재료 및 전자 부재 | |
JP5181769B2 (ja) | エポキシ樹脂組成物、及びその硬化物 | |
JP5382761B2 (ja) | エポキシ樹脂、エポキシ樹脂組成物、これを用いたプリプレグ及び積層板 | |
WO2016052290A1 (ja) | エポキシ樹脂組成物及びその硬化物 | |
JP4716082B2 (ja) | エポキシ樹脂組成物及びその硬化物 | |
TWI739976B (zh) | 含烯基之樹脂、硬化性樹脂組成物及其硬化物 | |
JP4474891B2 (ja) | エポキシ樹脂組成物、その硬化物及びエポキシ樹脂 | |
JP4844796B2 (ja) | 1液型エポキシ樹脂組成物及びその硬化物 | |
TW201902714A (zh) | 環氧樹脂、製造方法、環氧樹脂組成物及其硬化物 | |
KR20230052965A (ko) | 에폭시 수지 조성물, 접착 필름, 프린트 배선판, 반도체 칩 패키지, 반도체 장치, 및 접착 필름의 사용 방법 | |
JP4363048B2 (ja) | エポキシ樹脂組成物及びその硬化物 | |
JP4474890B2 (ja) | エポキシ樹脂組成物、その硬化物及び多価ヒドロキシ化合物 | |
JP2006257137A (ja) | エポキシ樹脂組成物及びその硬化物 | |
JP2005307032A (ja) | 1液型エポキシ樹脂組成物及びその硬化物 | |
JP2005314656A (ja) | 熱硬化性組成物及びその硬化物 | |
JP4567132B2 (ja) | エポキシ樹脂組成物 | |
JP4665444B2 (ja) | エポキシ樹脂の製造方法 | |
JP4984385B2 (ja) | エポキシ樹脂組成物およびその硬化物 | |
JP4766295B2 (ja) | エポキシ樹脂組成物及びこれを用いた積層板 | |
JP2002187933A (ja) | 変性エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 | |
JP4656374B2 (ja) | エポキシ樹脂組成物及びその硬化物 | |
JPWO2017026396A1 (ja) | エポキシ樹脂、変性エポキシ樹脂、エポキシ樹脂組成物およびその硬化物 | |
JP4356005B2 (ja) | 硬化性樹脂組成物及びそれを用いた硬化物 | |
JP4670269B2 (ja) | エポキシ樹脂組成物及びその硬化物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD01 | Notification of change of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7421 Effective date: 20050909 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070419 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100127 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100415 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100614 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100928 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101119 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110303 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110316 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4716082 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140408 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |