JP2010007124A - 銀含有粉体の製造方法、銀含有粉体及びその分散液 - Google Patents
銀含有粉体の製造方法、銀含有粉体及びその分散液 Download PDFInfo
- Publication number
- JP2010007124A JP2010007124A JP2008167262A JP2008167262A JP2010007124A JP 2010007124 A JP2010007124 A JP 2010007124A JP 2008167262 A JP2008167262 A JP 2008167262A JP 2008167262 A JP2008167262 A JP 2008167262A JP 2010007124 A JP2010007124 A JP 2010007124A
- Authority
- JP
- Japan
- Prior art keywords
- silver
- containing powder
- compound
- dispersion
- molecular weight
- 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
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 148
- 239000004332 silver Substances 0.000 title claims abstract description 148
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims abstract description 142
- 239000000843 powder Substances 0.000 title claims abstract description 135
- 239000006185 dispersion Substances 0.000 title claims abstract description 87
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- 239000007788 liquid Substances 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 239000003822 epoxy resin Substances 0.000 claims abstract description 47
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 47
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229920002873 Polyethylenimine Polymers 0.000 claims abstract description 38
- 239000003960 organic solvent Substances 0.000 claims abstract description 31
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 30
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000012736 aqueous medium Substances 0.000 claims abstract description 19
- 229940100890 silver compound Drugs 0.000 claims abstract description 13
- 150000003379 silver compounds Chemical class 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 239000012141 concentrate Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims description 36
- 239000002245 particle Substances 0.000 claims description 25
- 238000001035 drying Methods 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 238000003917 TEM image Methods 0.000 claims description 7
- 238000004108 freeze drying Methods 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 59
- 230000002829 reductive effect Effects 0.000 abstract description 20
- 230000004927 fusion Effects 0.000 abstract description 4
- 238000004321 preservation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 239000007787 solid Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- 229910052751 metal Inorganic materials 0.000 description 24
- 239000002184 metal Substances 0.000 description 24
- 238000003860 storage Methods 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000010408 film Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003638 chemical reducing agent Substances 0.000 description 14
- 239000010419 fine particle Substances 0.000 description 14
- 238000006722 reduction reaction Methods 0.000 description 14
- -1 silver ions Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000005259 measurement Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- 239000008139 complexing agent Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 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 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000002082 metal nanoparticle Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000007710 freezing Methods 0.000 description 6
- 230000008014 freezing Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000502 dialysis Methods 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 239000003223 protective agent Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 229910001923 silver oxide Inorganic materials 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000009776 industrial production Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 239000002932 luster Substances 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000012776 electronic material Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000003672 processing method Methods 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000009210 therapy by ultrasound Methods 0.000 description 3
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- ASQQEOXYFGEFKQ-UHFFFAOYSA-N dioxirane Chemical compound C1OO1 ASQQEOXYFGEFKQ-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009881 electrostatic interaction Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 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
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 229920001477 hydrophilic polymer Polymers 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-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 1
- 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 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- YFWIACABGHWPLP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;propane-1,2,3-triol Chemical compound OCC(O)CO.OCCOCCO YFWIACABGHWPLP-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NSPGLQRXIWDSEQ-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)O.[Ag]=O Chemical compound C(C1=CC=CC=C1)(=O)O.[Ag]=O NSPGLQRXIWDSEQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229910001111 Fine metal Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- PTYMQUSHTAONGW-UHFFFAOYSA-N carbonic acid;hydrazine Chemical compound NN.OC(O)=O PTYMQUSHTAONGW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HZZUMXSLPJFMCB-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;acetate Chemical compound CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 HZZUMXSLPJFMCB-UHFFFAOYSA-M 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 238000000879 optical micrograph Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229940071575 silver citrate Drugs 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- WYCFMBAHFPUBDS-UHFFFAOYSA-L silver sulfite Chemical compound [Ag+].[Ag+].[O-]S([O-])=O WYCFMBAHFPUBDS-UHFFFAOYSA-L 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- CHACQUSVOVNARW-LNKPDPKZSA-M silver;(z)-4-oxopent-2-en-2-olate Chemical compound [Ag+].C\C([O-])=C\C(C)=O CHACQUSVOVNARW-LNKPDPKZSA-M 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- XAYJXAUUXJTOSI-UHFFFAOYSA-M silver;2,2,3,3,3-pentafluoropropanoate Chemical compound [Ag+].[O-]C(=O)C(F)(F)C(F)(F)F XAYJXAUUXJTOSI-UHFFFAOYSA-M 0.000 description 1
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 1
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 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 1
- QUTYHQJYVDNJJA-UHFFFAOYSA-K trisilver;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Ag+].[Ag+].[Ag+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QUTYHQJYVDNJJA-UHFFFAOYSA-K 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Images
Landscapes
- Non-Insulated Conductors (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Manufacture Of Metal Powder And Suspensions Thereof (AREA)
- Powder Metallurgy (AREA)
- Conductive Materials (AREA)
Abstract
【解決手段】 (1)ポリエチレンイミン中のアミノ基にポリエチレングリコールが結合してなる化合物(X)、またはポリエチレンイミン中のアミノ基にポリエチレングリコールとエポキシ樹脂とが結合してなる化合物(Y)の存在下、水性媒体中で、銀化合物を銀ナノ粒子(Z)に還元する工程、(2)化合物(X)又は化合物(Y)と、銀ナノ粒子(Z)と、水性媒体との混合物に有機溶剤を加えて遠心濃縮する工程、(3)(2)で得られた濃縮物を乾燥する工程とを有することを特徴とする銀含有粉体の製造方法、該方法で得られる銀含有粉体、これを再分散させた分散液。
【選択図】 図3
Description
(1)数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に数平均分子量が500〜5,000のポリエチレングリコール(b)が結合してなる化合物(X)、または、
数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に、数平均分子量が500〜5,000のポリエチレングリコール(b)と、エポキシ樹脂(c)とが結合してなる化合物(Y)の存在下、水性媒体中で、銀化合物を銀ナノ粒子(Z)に還元する工程、
(2)(1)で得られた、化合物(X)又は化合物(Y)と、銀ナノ粒子(Z)と、水性媒体との混合物に有機溶剤を加え、その後濃縮する工程、
(3)(2)で得られた濃縮物を乾燥する工程
とを有することを特徴とする銀含有粉体の製造方法、及び該製造方法で得られる平均粒子径が2〜50nmの銀ナノ粒子を95質量%以上で含有する銀含有粉体を提供するものである。
(1)数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に数平均分子量が500〜5,000のポリエチレングリコール(b)が結合してなる化合物(X)、または、
数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に、数平均分子量が500〜5,000のポリエチレングリコール(b)と、エポキシ樹脂(c)とが結合してなる化合物(Y)の存在下、水性媒体中で、銀化合物を銀ナノ粒子(Z)に還元する工程、
(2)(1)で得られた、化合物(X)又は化合物(Y)と、銀ナノ粒子(Z)と、水性媒体との混合物に有機溶剤を加え、その後濃縮する工程、
(3)(2)で得られた濃縮物を乾燥する工程
とを有することを特徴とする。
窒素雰囲気下、メトキシポリエチレングリコール[Mn=2,000]20.0g(10.0mmol)、ピリジン8.0g(100.0mmol)、クロロホルム20mlの混合溶液に、p−トルエンスルホン酸クロライド9.6g(50.0mmol)を含むクロロホルム(30ml)溶液を、氷冷撹拌しながら30分間滴下した。滴下終了後、浴槽温度40℃でさらに4時間攪拌した。反応終了後、クロロホルム50mlを加えて反応液を希釈した。引き続き、5%塩酸水溶液100ml、飽和炭酸水素ナトリウム水溶液100ml、そして飽和食塩水溶液100mlで順次に洗浄した後、硫酸マグネシウムで乾燥し、濾過、減圧濃縮した。得られた固形物をヘキサンで数回洗浄した後、濾過、80℃で減圧乾燥して、トシル化された生成物22.0gを得た。
1H−NMR(CDCl3)測定結果:
δ(ppm):7.82(d),7.28(d),3.74〜3.54(bs),3.41(s),2.40(s)
1H−NMR(CDCl3)測定結果:
δ(ppm):3.50(s),3.05〜2.20(m)
ビスフェノールA型エポキシ樹脂EPICLON AM−040−P(DIC工業株式会社製、エポキシ当量933)18.7g(20m当量)、4−フェニルフェノール1.28g(7.5mmol)、65%酢酸エチルトリフェニルホスホニウムエタノール溶液0.26ml(0.12mol%)及びN,N−ジメチルアセトアミド50mlを、窒素雰囲気下、120℃で6時間反応させた。放冷後、水150ml中に滴下し、得られた沈殿物をメタノールで2回洗浄した後、60℃で減圧乾燥して、単官能性のエポキシ樹脂を得た。得られた生成物の収量は19.6g、収率は98%であった。
1H−NMR(CDCl3)測定結果:
δ(ppm):7.55〜6.75(m),4.40〜3.90(m),3.33(m),2.89(m),2.73(m),1.62(s)
合成例1で得た化合物(X−1)を0.592g用いた水溶液138.8gに酸化銀10.0gを加えて25℃で30分間攪拌した。引き続き、ジメチルエタノールアミン46.0gを攪拌しながら徐々に加えたところ、反応溶液は黒赤色に変わり、若干発熱したが、そのまま放置して25℃で30分間攪拌した。その後、10%アスコルビン酸水溶液15.2gを攪拌しながら徐々に加えた。その温度を保ちしながらさらに20時間攪拌を続けて、黒赤色の分散体を得た。
保存安定性:分散液を5℃冷蔵庫に3ヶ月保存後、銀ナノ粒子の透過型電子顕微鏡写真から得られる平均粒子径及び透過型電子顕微鏡写真での形状を比較。
合成例2で得た化合物(Y)を0.263g用いた水溶液77.0gにジメチルエタノールアミン23.0gを攪拌しながら徐々に加えたところ、若干発熱した。引き続き、反応温度を45℃にして硝酸銀5.0gに徐々に加えたところ、反応溶液は黒赤色に変わった。その後、反応温度を50℃にして4.5時間攪拌して反応を終了し、黒赤色の分散体を得た。
化合物(X−1)の代わりに分岐ポリエチレンイミン(日本触媒株式会社製、SP−200)0.474gを用いた他は実施例1と同様にして銀含有粉体を得ようとした。反応温度を保ちながら攪拌を続けていたが、反応時間と共に沈殿が生じ、銀ナノ粒子の分散体は得られなかった。該沈殿は金属光沢を有し、水または極性溶剤中でも分散せず、銀ナノ粒子特有のプラズモン吸収は観測されなかった。
化合物(Y−1)の代わりに分岐ポリエチレンイミン(日本触媒株式会社製、SP−200)0.210gを用いた他は実施例2と同様にして銀含有粉体を得ようとした。反応温度を保ちながら攪拌を続けていたが、反応時間と共に沈殿が生じ、銀ナノ粒子の分散体は得られなかった。該沈殿は金属光沢を有し、水または極性溶剤中でも分散せず、銀ナノ粒子特有のプラズモン吸収は観測されなかった。
上記の実施例1の工程(1)で得られた分散液に有機溶剤を用いた遠心濃縮工程を経ずに、すぐに凍結乾燥工程を行った。水量が多いため、凍結乾燥するに約10日間掛かるものの乾燥粉体ではなく粘土状の塊になった。得られた粘土状の銀含有固体を用いて実施例1同様に蒸留水に3時間攪拌して再分散させて固形分率20%の分散液を調製し、スピンコーターを使ってスライドグラス上に700rpmで30秒スピンコートして薄膜にしたが、製膜性の良い薄膜にならなかった。これをホットプレート上で180℃、30分間加熱し、フィルムの体積抵抗率を三菱化学株式会社製「低抵抗率計ロレスタEP」で測定したところ、オーバレンジ(O.L.測定不能)であった。
上記の実施例2の工程(1)より得られた黒赤色の分散液に有機溶剤を用いた遠心濃縮工程を経ずに、すぐに凍結乾燥工程を行った。水量が多いため、凍結乾燥するに約5日間掛かるものの乾燥粉体ではなく高粘性の塊になった。得られた高粘性塊の銀含有固形物を用いて実施例2同様に蒸留水に3時間攪拌して再分散させて固形分率30%の分散液を調製し、スピンコーターを使ってスライドグラス上に700rpmで30秒スピンコートして薄膜にしたが、製膜性の良い薄膜にならなかった。これをホットプレート上で180℃、30分間加熱し、フィルムの体積抵抗率を三菱化学株式会社製「低抵抗率計ロレスタEP」で測定したところ、オーバレンジ(O.L.測定不能)であった。
実施例2の工程(1)で得られた黒赤色の分散液中の硝酸イオンを除去するために、得られた分散体100gを透析チューブ(RVDF 500,000、スペクトラ社製)に入れて2.5Lの水中に約16時間水交換を3回繰り返して行った。引き続き、透析液を用いて2回繰り返し遠心分離(8000回転、5分)して、固形分50%に濃縮されたペースト状の銀含有粉体を得た。処理時間は実施例2の約1時間以下に比べて、合計で約55時間かかり、後処理工程中で発生した廃液量は実施例2の30倍以上であった。これらのことから、本発明の製造方法は、後処理工程が容易で、工業的に実用性の高い銀含有粉体の製造方法であることが明白である。
Claims (9)
- (1)数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に数平均分子量が500〜5,000のポリエチレングリコール(b)が結合してなる化合物(X)、または、
数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に、数平均分子量が500〜5,000のポリエチレングリコール(b)と、エポキシ樹脂(c)とが結合してなる化合物(Y)の存在下、水性媒体中で、銀化合物を銀ナノ粒子(Z)に還元する工程、
(2)(1)で得られた、化合物(X)又は化合物(Y)と、銀ナノ粒子(Z)と、水性媒体との混合物に有機溶剤を加え、その後濃縮する工程、
(3)(2)で得られた濃縮物を乾燥する工程
とを有することを特徴とする銀含有粉体の製造方法。 - 前記(3)の乾燥工程が凍結乾燥である請求項1記載の銀含有粉体の製造方法。
- 数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に数平均分子量が500〜5,000のポリエチレングリコール(b)が結合してなる化合物(X)、または、
数平均分子量が500〜50,000のポリエチレンイミン(a)中のアミノ基に、数平均分子量が500〜5,000のポリエチレングリコール(b)と、エポキシ樹脂(c)とが結合してなる化合物(Y)が、
透過型電子顕微鏡写真から求められる平均粒子径が2〜50nmの銀ナノ粒子(Z)の表面を被覆してなる銀含有粉体であって、
該銀含有粉体中の銀含有率が95質量%以上であることを特徴とする銀含有粉体。 - 示差走査熱量測定で求められる融点が100〜200℃の範囲である請求項3記載の銀含有粉体。
- 前記銀含有粉体が、乾燥状態では凝集しており、且つ溶剤(I)の存在下では分散するものである請求項3または4記載の銀含有粉体。
- 前記溶剤(I)が、ヒドロキシ基含有溶剤である請求項5記載の銀含有粉体。
- 請求項3〜6の何れか一項に記載の銀含有粉体を溶剤(I)に分散させてなることを特徴とする銀含有粉体の分散液。
- 銀含有粉体の濃度が20〜60質量%である請求項7記載の銀含有粉体の分散液。
- 請求項3〜6の何れか一項に記載の銀含有粉体を用いて得られることを特徴とする導電性ペースト。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008167262A JP4573138B2 (ja) | 2008-06-26 | 2008-06-26 | 銀含有粉体の製造方法、銀含有粉体及びその分散液 |
PCT/JP2009/060587 WO2009157309A1 (ja) | 2008-06-26 | 2009-06-10 | 銀含有粉体とその製法、これを用いる導電性ペーストとプラスチック基板 |
KR1020107020662A KR101239816B1 (ko) | 2008-06-26 | 2009-06-10 | 은 함유 분체의 제조 방법, 은 함유 분체, 도전성 페이스트 및 플라스틱 기판 |
CN200980123935.6A CN102066024B (zh) | 2008-06-26 | 2009-06-10 | 含银粉末及其制法、使用其的导电性糊剂和塑料基板 |
US12/737,220 US20110180764A1 (en) | 2008-06-26 | 2009-06-10 | Silver-containing powder, method for producing the same, conductive paste using the same, and plastic substrate |
EP09770019.9A EP2305402B1 (en) | 2008-06-26 | 2009-06-10 | Method for producing silver-containing powder and conductive paste using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008167262A JP4573138B2 (ja) | 2008-06-26 | 2008-06-26 | 銀含有粉体の製造方法、銀含有粉体及びその分散液 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010007124A true JP2010007124A (ja) | 2010-01-14 |
JP2010007124A5 JP2010007124A5 (ja) | 2010-03-25 |
JP4573138B2 JP4573138B2 (ja) | 2010-11-04 |
Family
ID=41587934
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008167262A Active JP4573138B2 (ja) | 2008-06-26 | 2008-06-26 | 銀含有粉体の製造方法、銀含有粉体及びその分散液 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4573138B2 (ja) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MD4075C1 (ro) * | 2009-12-31 | 2011-07-31 | Анатолий ЭФКАРПИДИС | Procedeu de obţinere a argintului coloidal de înaltă dispersie |
JP2014034495A (ja) * | 2012-08-09 | 2014-02-24 | Kawamura Institute Of Chemical Research | 金属酸化物ナノ構造体及びその製造方法 |
JP2014189896A (ja) * | 2013-03-28 | 2014-10-06 | Mitsubishi Materials Corp | 貴金属焼結体用の粘土状組成物 |
JP2014196556A (ja) * | 2013-03-07 | 2014-10-16 | Dic株式会社 | 導電性材料の製造方法及び導電性材料 |
JP2014205905A (ja) * | 2013-03-19 | 2014-10-30 | Dic株式会社 | 導電性材料の製造方法及び導電性材料 |
WO2016136723A1 (ja) * | 2015-02-23 | 2016-09-01 | 株式会社フルヤ金属 | ナノ粒子の精製方法 |
WO2017195621A1 (ja) * | 2016-05-09 | 2017-11-16 | Dic株式会社 | フレキソ印刷用金属ナノ粒子インク及びそれを用いた積層体の製造方法 |
WO2017199833A1 (ja) * | 2016-05-17 | 2017-11-23 | Dic株式会社 | 無電解ニッケルめっき方法 |
JP2019014188A (ja) * | 2017-07-10 | 2019-01-31 | Dic株式会社 | 積層体、それを用いたプリント配線板、フレキシブルプリント配線板及び成形品 |
CN110014168A (zh) * | 2019-05-23 | 2019-07-16 | 深圳先进技术研究院 | 一种纳米银颗粒及其制备方法 |
CN113263183A (zh) * | 2021-04-09 | 2021-08-17 | 宁夏中色新材料有限公司 | 一种纳米银脂类分散液及其制备方法 |
CN114746270A (zh) * | 2019-12-24 | 2022-07-12 | Dic株式会社 | 层叠体、印刷配线板、可挠性印刷配线板、电磁波屏蔽体及成形品 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI819048B (zh) | 2018-08-23 | 2023-10-21 | 日商Dic股份有限公司 | 積層體、成形品、導電性圖案及電子電路 |
JP7044203B2 (ja) | 2019-10-10 | 2022-03-30 | Dic株式会社 | 積層体、成形品、プリント配線板及び電磁波シールド |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003013106A (ja) * | 2001-06-28 | 2003-01-15 | Ube Nitto Kasei Co Ltd | シリカ被覆金属系複合粉体の製造方法およびシリカ被覆金属系複合粉体 |
JP2003103158A (ja) * | 2001-09-28 | 2003-04-08 | Nippon Paint Co Ltd | 高濃度金属コロイド粒子溶液、その製造方法及び金属性被膜の形成方法 |
JP2006097097A (ja) * | 2004-09-30 | 2006-04-13 | Aica Kogyo Co Ltd | フェライト被覆金属磁性微粒子の製造方法 |
JP2007308797A (ja) * | 2006-05-18 | 2007-11-29 | Ranco Co Ltd | 金属性粉末の再生方法 |
JP2008037884A (ja) * | 2006-08-01 | 2008-02-21 | Dainippon Ink & Chem Inc | 金属ナノ粒子分散体とその製造方法 |
-
2008
- 2008-06-26 JP JP2008167262A patent/JP4573138B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003013106A (ja) * | 2001-06-28 | 2003-01-15 | Ube Nitto Kasei Co Ltd | シリカ被覆金属系複合粉体の製造方法およびシリカ被覆金属系複合粉体 |
JP2003103158A (ja) * | 2001-09-28 | 2003-04-08 | Nippon Paint Co Ltd | 高濃度金属コロイド粒子溶液、その製造方法及び金属性被膜の形成方法 |
JP2006097097A (ja) * | 2004-09-30 | 2006-04-13 | Aica Kogyo Co Ltd | フェライト被覆金属磁性微粒子の製造方法 |
JP2007308797A (ja) * | 2006-05-18 | 2007-11-29 | Ranco Co Ltd | 金属性粉末の再生方法 |
JP2008037884A (ja) * | 2006-08-01 | 2008-02-21 | Dainippon Ink & Chem Inc | 金属ナノ粒子分散体とその製造方法 |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MD4075C1 (ro) * | 2009-12-31 | 2011-07-31 | Анатолий ЭФКАРПИДИС | Procedeu de obţinere a argintului coloidal de înaltă dispersie |
JP2014034495A (ja) * | 2012-08-09 | 2014-02-24 | Kawamura Institute Of Chemical Research | 金属酸化物ナノ構造体及びその製造方法 |
JP2014196556A (ja) * | 2013-03-07 | 2014-10-16 | Dic株式会社 | 導電性材料の製造方法及び導電性材料 |
JP2014205905A (ja) * | 2013-03-19 | 2014-10-30 | Dic株式会社 | 導電性材料の製造方法及び導電性材料 |
JP2014189896A (ja) * | 2013-03-28 | 2014-10-06 | Mitsubishi Materials Corp | 貴金属焼結体用の粘土状組成物 |
WO2016136723A1 (ja) * | 2015-02-23 | 2016-09-01 | 株式会社フルヤ金属 | ナノ粒子の精製方法 |
WO2017195621A1 (ja) * | 2016-05-09 | 2017-11-16 | Dic株式会社 | フレキソ印刷用金属ナノ粒子インク及びそれを用いた積層体の製造方法 |
JPWO2017195621A1 (ja) * | 2016-05-09 | 2018-05-24 | Dic株式会社 | フレキソ印刷用金属ナノ粒子インクを用いた積層体の製造方法 |
KR20180101527A (ko) * | 2016-05-09 | 2018-09-12 | 디아이씨 가부시끼가이샤 | 플렉소 인쇄용 금속 나노 입자 잉크 및 그것을 사용한 적층체의 제조 방법 |
KR102119002B1 (ko) | 2016-05-09 | 2020-06-04 | 디아이씨 가부시끼가이샤 | 플렉소 인쇄용 금속 나노 입자 잉크 및 그것을 사용한 적층체의 제조 방법 |
WO2017199833A1 (ja) * | 2016-05-17 | 2017-11-23 | Dic株式会社 | 無電解ニッケルめっき方法 |
JP2019014188A (ja) * | 2017-07-10 | 2019-01-31 | Dic株式会社 | 積層体、それを用いたプリント配線板、フレキシブルプリント配線板及び成形品 |
CN110014168A (zh) * | 2019-05-23 | 2019-07-16 | 深圳先进技术研究院 | 一种纳米银颗粒及其制备方法 |
CN114746270A (zh) * | 2019-12-24 | 2022-07-12 | Dic株式会社 | 层叠体、印刷配线板、可挠性印刷配线板、电磁波屏蔽体及成形品 |
CN113263183A (zh) * | 2021-04-09 | 2021-08-17 | 宁夏中色新材料有限公司 | 一种纳米银脂类分散液及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP4573138B2 (ja) | 2010-11-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4573138B2 (ja) | 銀含有粉体の製造方法、銀含有粉体及びその分散液 | |
WO2009157309A1 (ja) | 銀含有粉体とその製法、これを用いる導電性ペーストとプラスチック基板 | |
JP6120124B2 (ja) | 銀ペースト及びこれを用いて得られる導電性成形加工物 | |
JP5651299B2 (ja) | 導電性成形加工物の製造方法、導電性成形加工物、及びこれに用いる銀ペースト | |
US8088437B2 (en) | Method for production of silver-containing nano-structure, and silver-containing nano-structure | |
Li et al. | A General and Efficient Route to Fabricate Carbon Nanotube‐Metal Nanoparticles and Carbon Nanotube‐Inorganic Oxides Hybrids | |
JP5531504B2 (ja) | 銀ナノ粒子を用いる接合体の製造方法、及び接合体 | |
JP2008045024A (ja) | 金属ナノ粒子分散体を用いて得られる成形加工物、金属積層板及び塗膜 | |
JP2009535497A (ja) | ナノ粒子、その製造方法、およびその用途 | |
WO2004078641A1 (en) | Metal nano-particles coated with silicon oxide and manufacturing method thereof | |
Mallakpour et al. | An eco-friendly approach for the synthesis of biocompatible poly (vinyl alcohol) nanocomposite with aid of modified CuO nanoparticles with citric acid and vitamin C: mechanical, thermal and optical properties | |
WO2014057976A1 (ja) | コア-シェル型シリカナノ粒子及びその製造方法、並びにこれを利用した中空シリカナノ粒子の製造方法及び該製法により得られる中空シリカナノ粒子 | |
Tao et al. | Modification of multi-wall carbon nanotube surfaces with poly (amidoamine) dendrons: synthesis and metal templating | |
JP5621950B2 (ja) | 有機無機複合シリカナノ粒子及びそれを有する分散液、並びにそれらの製造方法 | |
KR20150114552A (ko) | 금속 나노 입자 보호 폴리머, 금속 콜로이드 용액 및 그들의 제조 방법 | |
Shi et al. | Facile preparation of highly luminescent CdTe quantum dots within hyperbranched poly (amidoamine) s and their application in bio-imaging | |
JP4026664B1 (ja) | 金属ナノ粒子分散体、およびその製造方法 | |
JP6119348B2 (ja) | コア−シェル型シリカ複合粒子及びその製造方法 | |
JP5521536B2 (ja) | 金属製膜基板の製造方法及びフレキシブルプラスチック基板 | |
WO2007010937A1 (ja) | 針状表面微粒子及びその製造方法 | |
JP5617891B2 (ja) | コア−シェル型シリカナノ粒子及びその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100128 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100128 |
|
A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20100128 |
|
A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20100224 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100302 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100412 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20100608 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100615 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20100709 |
|
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: 20100722 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100804 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4573138 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130827 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130827 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 |