JP6468023B2 - 導電性材料および導電性組成物 - Google Patents
導電性材料および導電性組成物 Download PDFInfo
- Publication number
- JP6468023B2 JP6468023B2 JP2015058865A JP2015058865A JP6468023B2 JP 6468023 B2 JP6468023 B2 JP 6468023B2 JP 2015058865 A JP2015058865 A JP 2015058865A JP 2015058865 A JP2015058865 A JP 2015058865A JP 6468023 B2 JP6468023 B2 JP 6468023B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- ascorbic acid
- substituent
- salt
- copper powder
- 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
- 239000000203 mixture Substances 0.000 title claims description 66
- 239000004020 conductor Substances 0.000 title claims description 43
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 122
- 150000003839 salts Chemical class 0.000 claims description 79
- 125000001424 substituent group Chemical group 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 229920005989 resin Polymers 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 27
- 229920001187 thermosetting polymer Polymers 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 238000002844 melting Methods 0.000 claims description 21
- 230000008018 melting Effects 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims 3
- 150000000996 L-ascorbic acids Chemical class 0.000 description 83
- 238000000034 method Methods 0.000 description 51
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 50
- -1 maleic acid Chemical class 0.000 description 46
- 150000001875 compounds Chemical class 0.000 description 25
- 230000003647 oxidation Effects 0.000 description 25
- 238000007254 oxidation reaction Methods 0.000 description 25
- 229960005070 ascorbic acid Drugs 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 238000000576 coating method Methods 0.000 description 20
- 235000010323 ascorbic acid Nutrition 0.000 description 18
- 239000011668 ascorbic acid Substances 0.000 description 18
- 238000001035 drying Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000002245 particle Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 239000010949 copper Substances 0.000 description 16
- 229910052802 copper Inorganic materials 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 15
- 230000001603 reducing effect Effects 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 6
- 239000005751 Copper oxide Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910000431 copper oxide Inorganic materials 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 239000002211 L-ascorbic acid Substances 0.000 description 4
- 235000000069 L-ascorbic acid Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000007602 hot air drying Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical class CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000010947 wet-dispersion method Methods 0.000 description 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical class CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- 239000011718 vitamin C Substances 0.000 description 2
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- QGLKIVPNOUPWOW-UHFFFAOYSA-N 3,4-dihydroxy-2h-furan-5-one Chemical group OC1=C(O)C(=O)OC1 QGLKIVPNOUPWOW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical class CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(C)[n+](*)c(C)[n]1* Chemical compound Cc1c(C)[n+](*)c(C)[n]1* 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000005075 adamantyloxy group Chemical group C12(CC3CC(CC(C1)C3)C2)O* 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 239000004318 erythorbic acid Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000007759 kiss coating Methods 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005295 norbornyloxy group Chemical group C12(CCC(CC1)C2)O* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 150000003864 primary ammonium salts Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003865 secondary ammonium salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Conductive Materials (AREA)
- Non-Insulated Conductors (AREA)
Description
X+は、下記一般式(2)で表されるカチオン、または、下記一般式(3)で表されるカチオンである。
R23〜R25は、それぞれ独立に、水素原子、置換基を有してよいアルキル基、置換基を有してよいアルケニル基、置換基を有してよいフェニル基、または、ハロゲン原子を表す。
ナス型フラスコに、L−アスコルビン酸(東京化成試薬)5.00g、ステアリルアミン(東京化成試薬)7.65g、脱水メタノール(関東化学試薬)150mlを混合し、40℃にて8時間撹拌したところ、淡黄色のスラリーが得られた。このスラリーを0℃まで冷却して濾過し、得られた固体を冷メタノール80mlで洗浄した。得られた固体を室温にて真空乾燥し、化合物B−1を淡黄色の固体として8.49g得た(収率67%)。
ナス型フラスコに、L−アスコルビン酸(東京化成試薬)5.00、脱水メタノール(関東化学試薬)50mlを加えて40℃で撹拌し、白色のスラリーを得た。この混合物に、トリヘキシルアミン(東京化成試薬)7.65gを数回に分けて添加し、40℃でさらに1時間撹拌したところ、不溶物はすべて溶解して淡黄色の溶液が得られた。ロータリーエバポレーターにて、この溶液から溶媒を留去し、室温で減圧乾燥することにより、化合物B−7を淡黄色の油状物として、12.59g得た(収率100%)。
化合物B−2〜B−6、B−8およびB−9は、上記、化合物B−7の合成方法において、トリヘキシルアミンを、それぞれの構造に対応するアミンに置き換え、L−アスコルビン酸に対して1.0モル当量を添加して、同様の操作を行うことで得ることができた。
ナス型フラスコに、L−アスコルビン酸(東京化成試薬)4.50g、脱水メタノール(関東化学試薬)100mlを加えて室温にて撹拌し、白色のスラリーを得た。このスラリーに、テトラブチルアンモニムヒドロキサイドの37wt%メタノール溶液(東京化成試薬)17.80gを約5分かけて滴下し、室温にてさらに1時間撹拌したところ無色の溶液が得られた。ロータリーエバポレーターにて、この溶液から溶媒を留去し、室温にて真空乾燥することにより、化合物B−10をほぼ無色の粘調な油状物として10.61g得た(収率99%)。
化合物B−11〜B−15は、上記化合物B−10の合成方法において、テトラブチルアンモニウムヒドロキサイドを、それぞれの化合物に対応するカチオンとヒドロキサイドからなる塩に置き換えた材料を用い、L−アスコルビン酸に対して1.0モル当量添加して同様の操作を行うことで、得ることができた。なお、化合物B−12〜B−15の原料として用いたヒドロキサイド塩は、Chemistry−A Europian Journal誌、14巻、5528〜5537頁(2008年)に記載の方法を参考に合成した。
化合物B−16〜B−20は、等モル当量の対応するアスコルビン酸誘導体と対応するアミンを原料に用い、化合物B−7の合成方法とほぼ同様の操作を行うことで、合成することができた。
(A−1)樹枝状銅粉FCC−2000(福田金属箔粉工業製、粒径D50=9.9μm)
(C−1)熱硬化性ウレタン樹脂(トーヨーケム社製/酸価=10mgKOH/g)
銅粉(A−1)を100重量部、アスコルビン酸誘導体の塩(B−1)2重量部、トルエン120重量部、直径1mmのガラスビーズ100重量部をマヨネーズ瓶に入れて、スキャンデックスにて5時間分散して、導電性材料の分散体を得た。ナイロンメッシュ(#50)を介してこの分散体からガラスビーズを除去した後、ろ過によって得られた固体を、室温にて真空乾燥することで、銅粉(A)とアスコルビン酸誘導体の塩(B)からなる導電性材料を得た。
次に、実施例1にで得られた導電性材料の導電性の評価を実施した。具体的には、粉体抵抗率測定システム(三菱化学アナリテック製)のプローブユニットに導電性材料の粉体3.0gを入れ、3MPaの圧力を加えた際の体積低効率を測定したところ、6×10-4Ωcmの良好な初期導電性が確認され、分散行程中の酸化が抑止されていることが確認できた。
さらに、上記で得られた実施例1の導電性材料をシャーレに入れ、大気中、150℃に設定した熱風乾燥オーブンSPHH−202(エスペック社製)中で30分加熱し、室温まで放冷した。その後、先に述べた方法と同様に、導電性材料の粉体の体積抵抗率を測定したところ、9×10-3Ωcmであった。
実施例1で得られた導電性材料をシャーレに入れ、温度85℃、湿度85%に設定した高温恒湿器LHL−114(エスペック社製)中に30分間保管し、デシケーター中で室温まで放冷した後、先に述べた方法と同様に、粉体の体積抵抗率を測定したところ、9×10-3Ωcmであった。
アスコルビン酸誘導体の塩(B)を表2に記載した材料と添加量に変更した他は、実施例1と同様の手順により、本発明の導電性材料を調製した。さらに、先に述べた方法で、粉体の初期導電性、すなわち、体積抵抗率を測定した。さらに、空気中−加熱化での保管試験後、高温高湿下での保管試験後の体積抵抗率もそれぞれ測定した。結果を表2に示した。
実施例1で得られた導電性材料の初期の粒子表面の状態、および、空気中−加熱下での保存試験後の粒子表面の状態を走査型電子顕微鏡S−4300(HITACHI製)にて加速電圧5kV、2500倍に観察した像を図(1)と図(2)にそれぞれ示した。図(1)から、樹枝状銅粉(A−1)がフレーク状に扁平化し、さらに、表面にアスコルビン酸誘導体(B−1)の微粒子が直接、接して存在していることが確認された。また、図(2)から、空気中−加熱下での保管試験後には、先のアスコルビン酸誘導体(B−1)の粒子液状化して銅表面に広がったことが確認できた。
ウレタン樹脂(C−1)を100重量部、実施例1で得たアスコルビン酸誘導体の塩(B−1)で被覆された導電性材料を300重量部、添加剤としてデカメチレンカルボン酸ジサリチロイルヒドラジド(アデカスタブCDA−6、ADEKA社)4.5重量部をガラス容器に仕込み、不揮発性分が40%となるように、トルエンとイソプロピルアルコールの混合溶媒(体積比9:1)を加えた。この混合物をディスパーで5分間撹拌を行うことで、導電性組成物を得た。
上記で得た膜状の導電性組成物の積層体を縦横共に25mmの正方形に切り出し、横25mm、縦100mm、厚み0.5mmのステンレス板の端部に、導電性組成物の面がステンレス板と向かいあうように置き、80℃、2MPaの条件で仮圧着した。その後、ポリエチレンテレフタレートのフィルムを剥離し、新たに露出した導電性組成物の面に、先と同じ大きさのステンレス板を図(5)に示した構成になるように重ねて置き、再度、80℃、2MPaの条件で仮圧着した。これを150℃、2MPaの条件で30分間、熱圧着することで、導電性組成物の導電性評価のための評価サンプルとした。
上記、評価サンプルを温度85℃、湿度85%に設定した高温高湿下に7日間保管した後、上記と同様の方法にて、抵抗値を測定した。結果を表3に示した。
導電性材料を表3に記載した導電性材料に変更した他は、実施例24と全く同様の方法にて得た評価サンプルに対して、抵抗値の測定を実施した。さらに、これらの評価サンプルを上記と同様の高温高湿下での保管試験を実施し、抵抗値を測定した結果も表3に併せて示した。
ウレタン樹脂(C−1)を100重量部、添加剤としてデカメチレンカルボン酸ジサリチロイルヒドラジド(アデカスタブCDA−6、ADEKA社)4.5重量部をガラス容器に仕込み、最終の不揮発性分が40%となるようにトルエンとイソプロピルアルコールの混合溶媒(体積比9:1)を加え、ディスパーで5分間撹拌した。次いで、銅粉(A−1)を300重量部、表4に示したアスコルビン酸誘導体の塩(B)を同表に記載の重量部で加え、さらに5分間、ディスパーで撹拌し、導電性組成物を得た。
2:ステンレス板
3:ステンレス板
4:導電性の評価において、電極を接触させる部分
5:導電性の評価において、電極を接触させる部分
Claims (4)
- 銅粉(A)と、下記一般式(1)で表されるアスコルビン酸誘導体の塩(B)とを含む導電性材料。
一般式(1)
(式中、R1およびR2は、それぞれ独立に、水素原子または置換基を有してよいアシル基を表す。
X+は、下記一般式(2)で表されるカチオン、または、下記一般式(3)で表されるカチオンである。)
一般式(2)
(式中、R11〜R14は、それぞれ独立に、水素原子、置換基を有してよいアルキル基、置換基を有してよいアルケニル基、または、置換基を有してよいアリール基を表すが、R11〜R14のうちの少なくとも1つは、置換基を有してよいアルキル基、置換基を有してよいアルケニル基、および、置換基を有してよいアリール基のいずれかである。また、R11〜R14は、隣接する置換基が一体となって、環構造を形成していてもよい。)
一般式(3)
(式中、R21およびR22は、それぞれ独立に、水素原子、置換基を有してよいアルキル基、置換基を有してよいアルケニル基、または、置換基を有してよいフェニル基を表す。
R23〜R25は、それぞれ独立に、水素原子、置換基を有してよいアルキル基、置換基を有してよいアルケニル基、置換基を有してよいフェニル基、または、ハロゲン原子を表す。) - アスコルビン酸誘導体の塩(B)の融点が150℃以下である請求項1に記載の導電性材料。
- 銅粉(A)が、アスコルビン酸誘導体の塩(B)で被覆されている、請求項1または2記載の導電性材料。
- 請求項1〜3いずれか記載の導電性材料と、熱硬化性樹脂(C)とを含む導電性組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015058865A JP6468023B2 (ja) | 2015-03-23 | 2015-03-23 | 導電性材料および導電性組成物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015058865A JP6468023B2 (ja) | 2015-03-23 | 2015-03-23 | 導電性材料および導電性組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016178047A JP2016178047A (ja) | 2016-10-06 |
JP6468023B2 true JP6468023B2 (ja) | 2019-02-13 |
Family
ID=57069343
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015058865A Active JP6468023B2 (ja) | 2015-03-23 | 2015-03-23 | 導電性材料および導電性組成物 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6468023B2 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11931808B2 (en) | 2018-08-08 | 2024-03-19 | Mitsui Mining & Smelting Co., Ltd. | Bonding composition, conductor bonding structure, and method for producing same |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59174661A (ja) * | 1983-03-23 | 1984-10-03 | Fukuda Kinzoku Hakufun Kogyo Kk | 導電塗料用銅粉 |
JPS62225573A (ja) * | 1986-03-28 | 1987-10-03 | Fukuda Metal Foil & Powder Co Ltd | 導電性ペ−スト用銅粉 |
JPS6414283A (en) * | 1987-07-07 | 1989-01-18 | Takeda Chemical Industries Ltd | Conductive paint composition |
JPH0371508A (ja) * | 1989-08-11 | 1991-03-27 | Nippon Oil & Fats Co Ltd | 銅系導電性ペースト |
JPH04242004A (ja) * | 1991-01-16 | 1992-08-28 | Sumitomo Bakelite Co Ltd | 導電性銅ペーストの製造方法 |
JPH04308605A (ja) * | 1991-04-08 | 1992-10-30 | Sumitomo Metal Ind Ltd | 銅導体ペースト |
JP3662715B2 (ja) * | 1997-06-16 | 2005-06-22 | アルプス電気株式会社 | 導電性材料および導電ペーストと電子機器 |
US20150380123A1 (en) * | 2013-03-01 | 2015-12-31 | Toda Kogyo Corp. | Process for producing conductive coating film, and conductive coating film |
-
2015
- 2015-03-23 JP JP2015058865A patent/JP6468023B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2016178047A (ja) | 2016-10-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2611347B2 (ja) | 銅系導電性塗料組成物 | |
EP3409729B1 (en) | Electroconductive composition, production process therefor, and electroconductive material | |
EP0162698B1 (en) | Solderable conductive compositions, methods for their preparation, and substrates coated with them | |
JP5320962B2 (ja) | 導電性組成物、導電性被膜の形成方法および導電性被膜 | |
WO2014089396A1 (en) | Linear-hyperbranched polymers as performance additives for solid electrolytic capacitors | |
WO2010074119A1 (ja) | 外部電極用導電性ペースト、及びそれを用いて形成した外部電極を有する積層セラミック電子部品 | |
JPS63165457A (ja) | 導電性樹脂組成物 | |
JPWO2012102304A1 (ja) | 導電性ペースト及びその製造方法 | |
KR20130110389A (ko) | 인쇄용 구리 페이스트 조성물 및 이를 이용한 금속패턴의 형성방법 | |
EP0326737A2 (en) | Copper powder for electroconductive paints and electroconductive paint compositions | |
Yong et al. | Use of decomposable polymer-coated submicron Cu particles with effective additive for production of highly conductive Cu films at low sintering temperature | |
US9982154B2 (en) | Solid ink composition | |
JP4339919B2 (ja) | 導電性組成物、導電性被膜の形成方法および導電性被膜 | |
JP6468023B2 (ja) | 導電性材料および導電性組成物 | |
CN107636055B (zh) | 金属纳米粒子分散体 | |
US4499010A (en) | Conductive paint | |
JP6530512B2 (ja) | 金属ナノ粒子の分散物 | |
DE102007017005B4 (de) | Elektrisch leitende Zusammensetzung, Verfahren zur Herstellung eines elektrisch leitenden Films | |
EP4070896B1 (en) | Metal partilce composition, method for producing metal particle composition, and paste | |
JP6631352B2 (ja) | 反応物、導電性組成物、および、表面処理銅粉の製造方法 | |
CN109313959B (zh) | 绝缘材料和布线部件 | |
JP5293581B2 (ja) | 導電性組成物、導電性配線の形成方法および導電性配線 | |
JPH08241623A (ja) | 金属粉末及びこれを用いた導電ペースト | |
JP5320974B2 (ja) | 導電性組成物、導電性被膜付き基材およびその製造方法 | |
US11980935B2 (en) | Copper particles and method for producing same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180110 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20181211 |
|
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: 20181218 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20181231 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 6468023 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |