JP5180440B2 - 放熱材料 - Google Patents
放熱材料 Download PDFInfo
- Publication number
- JP5180440B2 JP5180440B2 JP2006043306A JP2006043306A JP5180440B2 JP 5180440 B2 JP5180440 B2 JP 5180440B2 JP 2006043306 A JP2006043306 A JP 2006043306A JP 2006043306 A JP2006043306 A JP 2006043306A JP 5180440 B2 JP5180440 B2 JP 5180440B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- direct bond
- bismaleimide
- integer
- divalent substituent
- 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.)
- Active
Links
- 239000000463 material Substances 0.000 title claims description 61
- 230000017525 heat dissipation Effects 0.000 title claims description 29
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 54
- 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 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 28
- -1 polysiloxane group Polymers 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000011342 resin composition Substances 0.000 claims description 13
- 125000006848 alicyclic heterocyclic group Chemical group 0.000 claims description 9
- 239000011256 inorganic filler Substances 0.000 claims description 9
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 229910003849 O-Si Inorganic materials 0.000 claims description 7
- 229910003872 O—Si Inorganic materials 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 7
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 5
- 239000004917 carbon fiber Substances 0.000 claims description 5
- 239000000395 magnesium oxide Substances 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims description 4
- UOBYKYZJUGYBDK-UHFFFAOYSA-M 2-naphthoate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-M 0.000 claims description 4
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 4
- 229910052582 BN Inorganic materials 0.000 claims description 4
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 4
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 4
- PUNFICOCZAPAJV-UHFFFAOYSA-N bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound C1CC2CCC1(C(=O)O)CC2 PUNFICOCZAPAJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 claims description 4
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 4
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910002804 graphite Inorganic materials 0.000 claims description 4
- 239000010439 graphite Substances 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 claims description 4
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 4
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 4
- 235000021286 stilbenes Nutrition 0.000 claims description 4
- CWLGEPSKQDNHIO-JOBJLJCHSA-N (e)-n-[(e)-benzylideneamino]-1-phenylmethanimine Chemical compound C=1C=CC=CC=1/C=N/N=C/C1=CC=CC=C1 CWLGEPSKQDNHIO-JOBJLJCHSA-N 0.000 claims description 3
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 claims description 3
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- OVZXISBUYCEVEV-OUKQBFOZSA-N [(e)-1-phenylprop-1-en-2-yl]benzene Chemical compound C=1C=CC=CC=1C(/C)=C/C1=CC=CC=C1 OVZXISBUYCEVEV-OUKQBFOZSA-N 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 claims description 3
- 229910003460 diamond Inorganic materials 0.000 claims description 3
- 239000010432 diamond Substances 0.000 claims description 3
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 claims description 3
- XBDNVPPAQQNVBW-UHFFFAOYSA-N phenyl naphthalene-2-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)OC1=CC=CC=C1 XBDNVPPAQQNVBW-UHFFFAOYSA-N 0.000 claims description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 3
- 229910001887 tin oxide Inorganic materials 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 2
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
- 239000003566 sealing material Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000010292 electrical insulation Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 101100058548 Felis catus BMI1 gene Proteins 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000011162 core material Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- BCHKIOWPKLJEKK-UHFFFAOYSA-N 4-(2,5-dioxopyrrol-1-yl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1N1C(=O)C=CC1=O BCHKIOWPKLJEKK-UHFFFAOYSA-N 0.000 description 3
- GAUXFYRABTWLKY-UHFFFAOYSA-N 4-[6-(4-hydroxyphenoxy)hexoxy]phenol Chemical compound C1=CC(O)=CC=C1OCCCCCCOC1=CC=C(O)C=C1 GAUXFYRABTWLKY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 1
- QRFDGBAUUBFCEQ-UHFFFAOYSA-N 1,1'-biphenyl cyanic acid Chemical group OC#N.C1=CC=CC=C1C1=CC=CC=C1 QRFDGBAUUBFCEQ-UHFFFAOYSA-N 0.000 description 1
- SAWCWRKKWROPRB-UHFFFAOYSA-N 1,1-dibromohexane Chemical compound CCCCCC(Br)Br SAWCWRKKWROPRB-UHFFFAOYSA-N 0.000 description 1
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 1
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 1
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
- ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- STMZGJLCKJFMLQ-UHFFFAOYSA-N 2-[3-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCCC(CCN)C1 STMZGJLCKJFMLQ-UHFFFAOYSA-N 0.000 description 1
- XUXZELZSNNYLRE-UHFFFAOYSA-N 2-[4-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCC(CCN)CC1 XUXZELZSNNYLRE-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 1
- LBPVOEHZEWAJKQ-UHFFFAOYSA-N 3-[4-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 LBPVOEHZEWAJKQ-UHFFFAOYSA-N 0.000 description 1
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 description 1
- NQZOFDAHZVLQJO-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 NQZOFDAHZVLQJO-UHFFFAOYSA-N 0.000 description 1
- UCQABCHSIIXVOY-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]phenoxy]aniline Chemical group NC1=CC=CC(OC=2C=CC(=CC=2)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 UCQABCHSIIXVOY-UHFFFAOYSA-N 0.000 description 1
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 1
- ILCGTNBULCHWOE-UHFFFAOYSA-N 4-[[4-aminobutyl(dimethyl)silyl]oxy-dimethylsilyl]butan-1-amine Chemical compound NCCCC[Si](C)(C)O[Si](C)(C)CCCCN ILCGTNBULCHWOE-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
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- KEUCYUPOICDBOG-UHFFFAOYSA-N [2-(aminomethyl)-5-bicyclo[2.2.1]heptanyl]methanamine Chemical compound C1C2C(CN)CC1C(CN)C2 KEUCYUPOICDBOG-UHFFFAOYSA-N 0.000 description 1
- IVGBGCPUDUTSHT-UHFFFAOYSA-N [3-(3-aminobenzoyl)phenyl]-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(C=CC=2)C(=O)C=2C=C(N)C=CC=2)=C1 IVGBGCPUDUTSHT-UHFFFAOYSA-N 0.000 description 1
- UVXIFYUJZWURAR-UHFFFAOYSA-N [3-(4-aminobenzoyl)phenyl]-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 UVXIFYUJZWURAR-UHFFFAOYSA-N 0.000 description 1
- OTKFKCIRTBTDKK-UHFFFAOYSA-N [3-(aminomethyl)-5-bicyclo[2.2.1]heptanyl]methanamine Chemical compound C1C(CN)C2C(CN)CC1C2 OTKFKCIRTBTDKK-UHFFFAOYSA-N 0.000 description 1
- KJGPUSGHNHJCNO-UHFFFAOYSA-N [4-(3-aminobenzoyl)phenyl]-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC(=CC=2)C(=O)C=2C=C(N)C=CC=2)=C1 KJGPUSGHNHJCNO-UHFFFAOYSA-N 0.000 description 1
- SNYVZKMCGVGTKN-UHFFFAOYSA-N [4-(4-cyanatophenoxy)phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OC1=CC=C(OC#N)C=C1 SNYVZKMCGVGTKN-UHFFFAOYSA-N 0.000 description 1
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- BBRLKRNNIMVXOD-UHFFFAOYSA-N bis[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 BBRLKRNNIMVXOD-UHFFFAOYSA-N 0.000 description 1
- LSDYQEILXDCDTR-UHFFFAOYSA-N bis[4-(4-aminophenoxy)phenyl]methanone Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 LSDYQEILXDCDTR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XSYZCZPCBXYQTE-UHFFFAOYSA-N cyclodecylcyclodecane Chemical compound C1CCCCCCCCC1C1CCCCCCCCC1 XSYZCZPCBXYQTE-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- CPSVXUSVVWYBEX-UHFFFAOYSA-N phenyl bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(CC2)CCC12C(=O)OC1=CC=CC=C1 CPSVXUSVVWYBEX-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- DBIWHDFLQHGOCS-UHFFFAOYSA-N piperidine;trifluoroborane Chemical compound FB(F)F.C1CCNCC1 DBIWHDFLQHGOCS-UHFFFAOYSA-N 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
(1)一般式(I)で表されるビスマレイミドの硬化物を少なくとも含有する放熱材料。
(2)一般式(II)で表されるビスマレイミドの硬化物を少なくとも含有する放熱材料。
(3)更に無機充填剤を含有するものである(1)又は(2)記載の放熱材料。
(4)無機充填剤が、酸化アルミニウム、窒化アルミニウム、弗化アルミニウム、弗化カルシウム、シリカ、窒化ケイ素、炭化ケイ素、窒化ホウ素、酸化マグネシウム、酸化ベリリウム、酸化スズ、グラファイト、炭素繊維、ダイヤモンドから選ばれる少なくとも一種である上記(3)記載の放熱材料。
(5)一般式(II)で表されるビスマレイミドを少なくとも含有する樹脂組成物。
(6)一般式(III)で表されるビスマレイミド。
また、本発明の放熱材料は、下記一般式(II)で表されるビスマレイミドの硬化物を少なくとも含有する放熱材料である。
4,4’−ジアミノジフェニルエーテル、4,4’−ジアミノベンゾフェノン、4,4’−ジアミノジフェニルメタン、2,2−ビス(4−アミノフェニル)プロパン、
1,3−ビス(3−アミノフェノキシ)ベンゼン、1,3−ビス(4−アミノフェノキシ)ベンゼン、1,4−ビス(3−アミノフェノキシ)ベンゼン、1,4−ビス(4−アミノフェノキシ)ベンゼン、1,3−ビス(3−アミノベンゾイル)ベンゼン、1,3−ビス(4−アミノベンゾイル)ベンゼン、1,4−ビス(3−アミノベンゾイル)ベンゼン、1,4−ビス(4−アミノベンゾイル)ベンゼン、4,4’−ビス(3−アミノフェノキシ)ビフェニル、4,4’−ビス(4−アミノフェノキシ)ビフェニル、ビス[4−(3−アミノフェノキシ)フェニル]ケトン、ビス[4−(4−アミノフェノキシ)フェニル]ケトン、ビス[4−(3−アミノフェノキシ)フェニル]エーテル、ビス[4−(4−アミノフェノキシ)フェニル]エーテル、2,2−ビス[4−(3−アミノフェノキシ)フェニル]プロパン、2,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン、
1,4−ジアミノシクロヘキサン、1,3−ジ(2−アミノエチル)シクロヘキサン、1,4−ジ(2−アミノエチル)シクロヘキサン、ビス(4−アミノシクロへキシル)メタン、2,6−ビス(アミノメチル)ビシクロ[2,2,1]ヘプタン、2,5−ビス(アミノメチル)ビシクロ[2,2,1]ヘプタン、ピペラジン等が挙げられる。
融点測定:示差走査熱量分析((株)パーキンエルマージャパン製;Pyris1 DSC)、昇温速度:5℃/min での測定し、吸熱のピークトップの温度を融点とした。
熱伝導率評価:熱伝導率は、定常法熱伝導率測定装置(アルバック理工(株)製GH−1)を用いて評価した。
吸湿率:85℃、85%RH 72hr後の試験片の重量変化より吸湿率を評価した。
機械強度評価:曲げ強度を、JIS−K6911に準じて評価した。
撹拌器、還流冷却器、滴下漏斗および窒素導入管を備えた容器に、エタノール1kg、ハイドロキノン(東京化成(株)製)616.62g、および次亜硫酸ナトリウム1.49gを装入した。これを撹拌しつつ、ジブロモヘキサン170.78gを添加し、昇温し混合溶液を還流させた。水酸化カリウム117.82gおよびエタノール500gから別途溶液を調製し、滴下漏斗を用いて、上記混合溶液に徐々に滴下した。撹拌しつつ還流を8時間継続した後、室温まで冷却した。30wt%に希釈した硫酸を加え、反応溶液を酸性にした後、エタノール500mLを加え白色沈殿をろ別した。白色沈殿は熱エタノールで1回洗浄した後、蒸留水で3回洗浄し、減圧下80℃で乾燥することで白色固体の4,4’−[1,6―ヘキサンジイルビス(オキシ)]ビスフェノールを得た。収量: 146.81g(69%)
上記非特許文献1(Macromol.Chem.Phys.,No.17,201(2000))に記載の、公知の方法により、4−マレイミドベンゾイル クロリドを合成した。
撹拌器、還流冷却器および窒素導入管を備えた容器に、4,4’−[1,6―ヘキサンジイルビス(オキシ)]ビスフェノール(合成品)30.24g、トリエチルアミン12.65gおよびTHF500gを装入し撹拌した。氷水浴で冷却しつつ、4−マレイミドベンゾイル クロリド(合成品) 70.68gを序々に装入した。氷水浴を外し室温まで昇温し、24時間撹拌を継続した。得られた暗褐色懸濁液をろ過し、褐色沈殿をろ別した。この褐色沈殿を蒸留水で3回洗浄し、減圧乾燥機を用いて100℃下で乾燥し、褐色固体のビスマレイミド(以下、BMI−1と略す)を得た。
融点:145.8℃
1H―NMR (270MHz,CDCl3):δ8.29(4H,d,芳香族)、7.58(4H,d,芳香族)、7.12(4H,d,芳香族)、6.93(4H,d,芳香族)、6.90(4H,s,不飽和)、3.99(4H,br,CH2)、1.84(4H,br,CH2)、1.56(4H,br,CH2)
BMI−1、および表1に示す構造のBMI−2、BMI−3、BMI−4を合成し、ジクミルパーオキサイド(シグマアルドリッチジャパン(株)製;以下、DCPO)、および窒化アルミニウム粉(三井化学(株)製;平均粒子径15μm、気孔率0.1%、真球度0.96)を表1の組成で添加し均一に混合した。放熱材料の作製には、熱プレス機((株)東洋精機製作所製ミニテストプレスMP-S)を用いた。上記樹脂組成物を、これを常温にて金型に装入し180℃、7時間で加熱硬化させることで、厚さ1mmの板状の放熱材料を作製した。結果を表1に示す。
BMI−1の代わりに、公知のビスマレイミドであるビス(4−マレイミドフェニル)メタン(合成品;以下BMI−0と略す)を用いる以外は、実施例1と同様の方法により、厚さ1mmの板状のビスマレイミド樹脂硬化物を作製した。結果を表1に示す。
公知のエポキシ樹脂モノマーである4―(オキシラニルメトキシ)ベンゾイックアシッド―4,4′―[1,6−ヘキサンジイルビス(オキシ)]ビスフェノールエステル(合成品;以下、EP−1と略す)、4,4′−ジアミノジフェニルエーテル(以下、DDEと略す)g、および窒化アルミニウム粉(三井化学(株)製;平均粒子径15μm、気孔率0.1%、真球度0.96)を表1の組成で添加し均一に混合し、これを金型に装入し、160℃、10時間で加熱硬化させることで、厚さ1mmのエポキシ樹脂硬化物を作製した。結果を表1に示す。
Claims (11)
- 一般式(II)で表されるビスマレイミドの硬化物を少なくとも含有する放熱材料。
xは、−CH2−、−Si(CH3)2−、または−O−の群から選び組み合わせることにより表される2乃至20個の原子団から構成される2価の置換基を示し、
yおよびzは、各々独立して直接結合、−O−、−CH2−CH2−、−CH=CH−、−C≡C−、−CO−、−CO−O−、−CO−NH−、−C(CH3)=CH−、−CH=N−、−CH=N−N=CH−、−N=N−または−N(O)=N−の群から選ばれる2価の置換基を示す) - 前記一般式(II)における−A2−z−A1−で表される基は、それぞれ、ビフェニル、ジフェニルエーテル、スチルベン、ジフェニルアセチレン、ベンゾフェノン、フェニルベンゾエート、フェニルベンズアミド、1,2-ジフェニルプロペン、N-ベンジリデンベンゼンアミン、1,2−ジベンジリデンヒドラジン、アゾベンゼン、2−ナフトエート、フェニル−2−ナフトエート、ビシクロ[2.2.2]オクタン-1-カルボキシレート、およびフェニルビシクロ[2.2.2]オクタン-1-カルボキシレートである、請求項1に記載の放熱材料。
- 前記一般式(II)におけるyが−O−、−CH2−CH2−、−CH=CH−、−C≡C−、−CO−、−CO−O−、−CO−NH−、−C(CH3)=CH−、−CH=N−、−CH=N−N=CH−、−N=N−または−N(O)=N−の群から選ばれる2価の置換基である場合、xは、−CH2−、−Si(CH3)2−、または−O−の群から選び組み合わせることにより表される2乃至20個の原子団から構成される2価の置換基を示し、
yがいずれも直接結合である場合、xは、−CH2−、−Si(CH3)2−、または−O−の群から少なくとも2種以上を選び組み合わせることにより表される2乃至20個の原子団から構成される2価の置換基を示す、請求項1または2に記載の放熱材料。 - 前記一般式(II)における−y−x−y−で表される基が、ケイ素数2乃至10のポリシロキサン基、炭素数2乃至10のポリオキシエチレン基、または−(CH2)n−Si(CH3)2−[O−Si(CH3)2]m−(CH2)n−で表される変性ポリシロキサン基、−O−(CH2)h−O−、−CO−NH−(CH2)i−NH−CO−、−CO−O−(CH2)i−O−CO−、−O−(CH2−CH2−O)k−、−CO−NH−(CH2)n−Si(CH3)2−[O−Si(CH3)2] m−(CH2)n−NH−CO−(hは1乃至20の整数、iは1乃至5の整数、kは1乃至10の整数、mは1乃至4の整数を示し、nは1乃至5の整数を示す)である、請求項1〜3のいずれか一項に記載の放熱材料。
- 更に、無機充填剤を含有するものである請求項1〜4のいずれか一項に記載の放熱材料。
- 無機充填剤が、酸化アルミニウム、窒化アルミニウム、弗化アルミニウム、弗化カルシウム、シリカ、窒化ケイ素、炭化ケイ素、窒化ホウ素、酸化マグネシウム、酸化ベリリウム、酸化スズ、グラファイト、炭素繊維、ダイヤモンドから選ばれる少なくとも一種である請求項5に記載の放熱材料。
- 一般式(III)で表されるビスマレイミド。
xは、−CH2−、−Si(CH3)2−、または−O−の群から選び組み合わせることにより表される2乃至20個の原子団から構成される2価の置換基を示し、
yは、直接結合、−O−、−CH2−CH2−、−CH=CH−、−C≡C−、−CO−、−CO−NH−、−C(CH3)=CH−、−CH=N−、−CH=N−N=CH−、−N=N−または−N(O)=N−の群から選ばれる2価の置換基を示し、
zは、直接結合、−O−、−CH2−CH2−、−CH=CH−、−C≡C−、−CO−、−CO−O−、−CO−NH−、−C(CH3)=CH−、−CH=N−、−CH=N−N=CH−、−N=N−または−N(O)=N−の群から選ばれる2価の置換基を示す) - 前記一般式(III)における−A2−z−A1−で表される基は、それぞれ、ビフェニル、ジフェニルエーテル、スチルベン、ジフェニルアセチレン、ベンゾフェノン、フェニルベンゾエート、フェニルベンズアミド、1,2-ジフェニルプロペン、N-ベンジリデンベンゼンアミン、1,2−ジベンジリデンヒドラジン、アゾベンゼン、2−ナフトエート、フェニル−2−ナフトエート、ビシクロ[2.2.2]オクタン-1-カルボキシレート、およびフェニルビシクロ[2.2.2]オクタン-1-カルボキシレートである、請求項7に記載のビスマレイミド。
- 前記一般式(III)におけるyが−O−、−CH2−CH2−、−CH=CH−、−C≡C−、−CO−、−CO−O−、−CO−NH−、−C(CH3)=CH−、−CH=N−、−CH=N−N=CH−、−N=N−または−N(O)=N−の群から選ばれる2価の置換基である場合、xは、−CH2−、−Si(CH3)2−、または−O−の群から選び組み合わせることにより表される2乃至20個の原子団から構成される2価の置換基を示し、
yがいずれも直接結合である場合、xは−CH2−、−Si(CH3)2−、または−O−の群から少なくとも2種以上を選び組み合わせることにより表される2乃至20個の原子団から構成される2価の置換基を示す、請求項7または8に記載のビスマレイミド。 - 前記一般式(III)における−y−x−y−で表される基が、ケイ素数2乃至10のポリシロキサン基、炭素数2乃至10のポリオキシエチレン基、または−(CH2)n−Si(CH3)2−[O−Si(CH3)2]m−(CH2)n−で表される変性ポリシロキサン基、−O−(CH2)h−O−、−CO−NH−(CH2)i−NH−CO−、−CO−O−(CH2)i−O−CO−、−O−(CH2−CH2−O)k−、−CO−NH−(CH2)n−Si(CH3)2−[O−Si(CH3)2] m−(CH2)n−NH−CO−(hは1乃至20の整数、iは1乃至5の整数、kは1乃至10の整数、mは1乃至4の整数を示し、nは1乃至5の整数を示す)である、請求項7〜9のいずれか一項に記載のビスマレイミド。
- 請求項7〜10のいずれか一項に記載の前記ビスマレイミドを少なくとも含有する樹脂組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006043306A JP5180440B2 (ja) | 2006-02-21 | 2006-02-21 | 放熱材料 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006043306A JP5180440B2 (ja) | 2006-02-21 | 2006-02-21 | 放熱材料 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007224060A JP2007224060A (ja) | 2007-09-06 |
JP5180440B2 true JP5180440B2 (ja) | 2013-04-10 |
Family
ID=38546165
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006043306A Active JP5180440B2 (ja) | 2006-02-21 | 2006-02-21 | 放熱材料 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5180440B2 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5117298B2 (ja) * | 2008-06-27 | 2013-01-16 | 株式会社イノアックコーポレーション | 射出成形用熱可塑性樹脂組成物と射出成形体 |
KR101618239B1 (ko) | 2008-10-30 | 2016-05-04 | 카네카 코포레이션 | 고열전도성의 열가소성 수지 조성물 및 열가소성 수지 |
KR101717449B1 (ko) | 2009-09-16 | 2017-03-17 | 카네카 코포레이션 | 유기 열전도성 첨가제,수지 조성물,및 경화제 |
WO2011132390A1 (ja) | 2010-04-19 | 2011-10-27 | 株式会社カネカ | 高熱伝導性熱可塑性樹脂 |
KR20130103310A (ko) | 2010-04-19 | 2013-09-23 | 카네카 코포레이션 | 고 열전도성 열가소성 수지 |
JP5392178B2 (ja) * | 2010-05-13 | 2014-01-22 | 日立化成株式会社 | 高熱伝導性複合粒子及びそれを用いた放熱材料 |
CN103370355B (zh) | 2011-02-08 | 2015-10-14 | 株式会社钟化 | 高热传导性热塑性树脂、树脂组合物及成形体 |
SG11202006971XA (en) * | 2018-01-22 | 2020-08-28 | Merck Patent Gmbh | Dielectric materials |
WO2021145414A1 (ja) * | 2020-01-16 | 2021-07-22 | リンテック株式会社 | 樹脂シート |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0782326A (ja) * | 1993-06-29 | 1995-03-28 | Mitsubishi Chem Corp | 封止用樹脂組成物 |
JPH07215933A (ja) * | 1994-01-28 | 1995-08-15 | Sumitomo Bakelite Co Ltd | ビスマレイミド化合物及びその製造方法 |
JP2002080617A (ja) * | 2000-09-06 | 2002-03-19 | Polymatech Co Ltd | 熱伝導性シート |
-
2006
- 2006-02-21 JP JP2006043306A patent/JP5180440B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2007224060A (ja) | 2007-09-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5180440B2 (ja) | 放熱材料 | |
CN106973490B (zh) | 硅氧烷化合物用于印刷布线板的用途 | |
JP6468465B2 (ja) | 樹脂組成物、プリプレグ、樹脂シート及び金属箔張り積層板 | |
US10323126B2 (en) | Siloxane compound, modified imide resin, thermosetting resin composition, prepreg, film with resin, laminated plate, multilayer printed wiring board, and semiconductor package | |
JP6886133B1 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 | |
JP2021021027A (ja) | マレイミド化合物及びその製造方法、アミド酸化合物及びその製造方法、樹脂組成物、硬化物、樹脂シート、プリプレグ、金属箔張積層板、プリント配線板、封止用材料、繊維強化複合材料、接着剤、並びに半導体装置 | |
JP2019189761A (ja) | 樹脂組成物、硬化物、単層樹脂シート、積層樹脂シート、プリプレグ、金属箔張積層板、プリント配線板、封止用材料、繊維強化複合材料及び接着剤 | |
KR101770546B1 (ko) | 프린트 배선판용 수지 조성물, 프리프레그, 수지 복합 시트 및 금속박 피복 적층판 | |
JP6994174B2 (ja) | 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板 | |
WO2013084819A1 (ja) | 樹脂組成物、プリプレグ及び積層板 | |
JP2008308551A (ja) | 新規ポリアミド酸、ポリイミド並びにその用途 | |
CN111601850A (zh) | 用于半导体封装的热固性树脂组合物、使用其的预浸料和金属包层层合体 | |
TWI700328B (zh) | 樹脂組成物、預浸體、樹脂片、覆金屬箔疊層板及印刷電路板 | |
JP2008308550A (ja) | 新規ポリアミド酸、ポリイミド並びにその用途 | |
JP6994171B2 (ja) | 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板 | |
TW200908820A (en) | Printed wiring board and electronic device | |
JPWO2020217672A1 (ja) | 硬化性樹脂組成物 | |
WO2019198626A1 (ja) | シアン酸エステル化合物、樹脂組成物、硬化物、単層樹脂シート、積層樹脂シート、プリプレグ、金属箔張積層板、プリント配線板、封止用材料、繊維強化複合材料、及び接着剤 | |
JP7191275B1 (ja) | 熱硬化性樹脂組成物、硬化物、樹脂シート、プリプレグ、金属箔張積層板、多層プリント配線板、封止用材料、繊維強化複合材料、接着剤及び半導体装置 | |
US9656443B2 (en) | Stable solution of ring-opened polymer and the use thereof | |
JP7057542B2 (ja) | 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板 | |
CN109825039B (zh) | 氰酸酯树脂组合物及其用途 | |
JP7154475B2 (ja) | プリント配線板用樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板 | |
TW202409181A (zh) | 樹脂組成物、預浸體、積層板、樹脂薄膜、印刷線路板及半導體封裝體 | |
JP5056657B2 (ja) | 回路基板用樹脂組成物、プリプレグおよび積層板 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080708 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20090216 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20090216 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110622 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110628 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110824 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120221 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120419 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120515 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120810 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20120928 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121023 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121204 |
|
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: 20130108 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130111 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5180440 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
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 |