JP4481568B2 - チオエーテル基含有接着剤および接着剤組成物 - Google Patents
チオエーテル基含有接着剤および接着剤組成物 Download PDFInfo
- Publication number
- JP4481568B2 JP4481568B2 JP2002571782A JP2002571782A JP4481568B2 JP 4481568 B2 JP4481568 B2 JP 4481568B2 JP 2002571782 A JP2002571782 A JP 2002571782A JP 2002571782 A JP2002571782 A JP 2002571782A JP 4481568 B2 JP4481568 B2 JP 4481568B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- epoxy
- sulfanyl
- thioether
- composition
- 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.)
- Expired - Lifetime
Links
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 161
- 239000000853 adhesive Substances 0.000 title claims abstract description 160
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 125000000101 thioether group Chemical group 0.000 title description 3
- 239000003822 epoxy resin Substances 0.000 claims abstract description 41
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 41
- 150000003568 thioethers Chemical class 0.000 claims abstract description 36
- 229920003023 plastic Polymers 0.000 claims abstract description 24
- 239000004033 plastic Substances 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000010703 silicon Substances 0.000 claims abstract description 17
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 17
- 229920001721 polyimide Polymers 0.000 claims abstract description 11
- 239000004642 Polyimide Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 239000000758 substrate Substances 0.000 claims description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 11
- -1 {3-[(6-{[3- (2-oxiranylmethoxy) propyl] sulfanyl} hexyl) sulfanyl] propoxy} methyl Chemical group 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- ULAPTGMUZMTLIJ-UHFFFAOYSA-N 2-[3-[2-[2-[3-(oxiran-2-ylmethoxy)propylsulfanyl]ethylsulfanyl]ethylsulfanyl]propoxymethyl]oxirane Chemical compound C1OC1COCCCSCCSCCSCCCOCC1CO1 ULAPTGMUZMTLIJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000007777 multifunctional material Substances 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 29
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 abstract description 19
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 abstract description 19
- 239000002904 solvent Substances 0.000 abstract description 18
- 239000004417 polycarbonate Substances 0.000 abstract description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 16
- 239000000377 silicon dioxide Substances 0.000 abstract description 14
- 229920000515 polycarbonate Polymers 0.000 abstract description 13
- 239000004926 polymethyl methacrylate Substances 0.000 abstract description 12
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 9
- 235000012239 silicon dioxide Nutrition 0.000 abstract description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052737 gold Inorganic materials 0.000 abstract description 3
- 239000010931 gold Substances 0.000 abstract description 3
- 229910000510 noble metal Inorganic materials 0.000 abstract description 2
- 229910052763 palladium Inorganic materials 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 29
- 239000000126 substance Substances 0.000 description 21
- 230000035882 stress Effects 0.000 description 20
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 239000000976 ink Substances 0.000 description 16
- 229920006332 epoxy adhesive Polymers 0.000 description 15
- 230000008961 swelling Effects 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- 230000009477 glass transition Effects 0.000 description 13
- 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 13
- 238000009472 formulation Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 10
- 229920001021 polysulfide Polymers 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 7
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000005065 mining Methods 0.000 description 6
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 239000000919 ceramic Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 3
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 3
- OYYIHDOYTDYIDZ-UHFFFAOYSA-N 2-[3-[2-[2-[2-[3-(oxiran-2-ylmethoxy)propylsulfanyl]ethoxy]ethoxy]ethylsulfanyl]propoxymethyl]oxirane Chemical compound C1OC1COCCCSCCOCCOCCSCCCOCC1CO1 OYYIHDOYTDYIDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 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
- 239000011449 brick Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- VLXBWPOEOIIREY-UHFFFAOYSA-N dimethyl diselenide Natural products C[Se][Se]C VLXBWPOEOIIREY-UHFFFAOYSA-N 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012994 photoredox catalyst Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-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
- 229910000547 2024-T3 aluminium alloy Inorganic materials 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 101100137008 Streptomyces hygroscopicus Pmms gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000002048 anodisation reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- 238000005237 degreasing agent Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- QEBJRRFIWCWPMA-UHFFFAOYSA-N diethyl-bis(sulfanyl)-$l^{4}-sulfane Chemical compound CCS(S)(S)CC QEBJRRFIWCWPMA-UHFFFAOYSA-N 0.000 description 1
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011104 metalized film Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920000434 poly[(mercaptopropyl)methylsiloxane] polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/302—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/16—Metal
- C09J2400/163—Metal in the substrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/20—Presence of organic materials
- C09J2400/22—Presence of unspecified polymer
- C09J2400/226—Presence of unspecified polymer in the substrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2463/00—Presence of epoxy resin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2479/00—Presence of polyamine or polyimide
- C09J2479/08—Presence of polyamine or polyimide polyimide
- C09J2479/086—Presence of polyamine or polyimide polyimide in the substrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2483/00—Presence of polysiloxane
- C09J2483/006—Presence of polysiloxane in the substrate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/801,234 US6800371B2 (en) | 2001-03-07 | 2001-03-07 | Adhesives and adhesive compositions containing thioether groups |
| PCT/US2002/003471 WO2002072725A1 (en) | 2001-03-07 | 2002-02-05 | Adhesives and adhesive compositions containing thioether groups |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004532299A JP2004532299A (ja) | 2004-10-21 |
| JP2004532299A5 JP2004532299A5 (enExample) | 2005-12-22 |
| JP4481568B2 true JP4481568B2 (ja) | 2010-06-16 |
Family
ID=25180543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002571782A Expired - Lifetime JP4481568B2 (ja) | 2001-03-07 | 2002-02-05 | チオエーテル基含有接着剤および接着剤組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6800371B2 (enExample) |
| EP (1) | EP1366130B1 (enExample) |
| JP (1) | JP4481568B2 (enExample) |
| KR (1) | KR100933964B1 (enExample) |
| AT (1) | ATE301174T1 (enExample) |
| DE (1) | DE60205342T2 (enExample) |
| MX (1) | MXPA03007929A (enExample) |
| MY (1) | MY128233A (enExample) |
| WO (1) | WO2002072725A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7622548B2 (en) * | 2003-07-11 | 2009-11-24 | Prc Desoto International, Inc. | Epoxy- or amine/hydroxy-capped polythioethers |
| US20050010003A1 (en) * | 2003-07-11 | 2005-01-13 | Prc-Desoto International, Inc. | Epoxy-capped polythioethers |
| US7183353B2 (en) * | 2004-04-29 | 2007-02-27 | Hewlett-Packard Development Company, L.P. | UV curable coating composition |
| US20070236542A1 (en) * | 2006-03-29 | 2007-10-11 | Graham David C | Adhesive Compositions, Micro-Fluid Ejection Devices, and Methods for Attaching Micro-Fluid Ejection Heads |
| US7553925B2 (en) * | 2006-05-05 | 2009-06-30 | Ppg Industries Ohio, Inc. | Thioether functional oligomeric polythiols and articles prepared therefrom |
| US8623989B1 (en) | 2006-05-05 | 2014-01-07 | PRC De Soto International, Inc. | Polyurea/polythiourea coatings |
| US7879955B2 (en) * | 2007-05-01 | 2011-02-01 | Rao Chandra B | Compositions including a polythioether |
| CN102112536B (zh) * | 2008-06-16 | 2015-06-24 | 3M创新有限公司 | 增韧可固化组合物 |
| EP2362394B1 (en) * | 2009-01-13 | 2018-11-21 | Panasonic Intellectual Property Management Co., Ltd. | Information recording device, information reproducing device, and information recording medium |
| US20110014354A1 (en) * | 2009-07-20 | 2011-01-20 | David Christopher Graham | Adhesive compositions and methods for use in failure analysis |
| US8785524B2 (en) | 2010-06-24 | 2014-07-22 | Funai Electric Co., Ltd. | Spray coatable adhesive for bonding silicon dies to rigid substrates |
| JP5960524B2 (ja) * | 2012-07-03 | 2016-08-02 | 株式会社Adeka | 含硫黄エポキシ化合物、該化合物を含有する樹脂組成物、及び、該樹脂組成物を含有する接着剤 |
| JP2014012778A (ja) * | 2012-07-05 | 2014-01-23 | Adeka Corp | 樹脂組成物及びそれを含有してなる接着剤 |
| EP3099496A4 (en) | 2014-01-29 | 2017-12-13 | Hewlett-Packard Development Company L.P. | Fluid directing assembly |
| WO2017004495A1 (en) | 2015-07-01 | 2017-01-05 | 3M Innovative Properties Company | Composite membranes with improved performance and/or durability and methods of use |
| EP3316997A1 (en) | 2015-07-01 | 2018-05-09 | 3M Innovative Properties Company | Pvp- and/or pvl-containing composite membranes and methods of use |
| WO2017004496A1 (en) | 2015-07-01 | 2017-01-05 | 3M Innovative Properties Company | Polymeric ionomer separation membranes and methods of use |
| TWI572675B (zh) * | 2015-07-15 | 2017-03-01 | 臻鼎科技股份有限公司 | 聚醯亞胺組合物、聚醯亞胺膜及電路板 |
| CN107621752B (zh) | 2016-07-13 | 2019-11-12 | 常州强力先端电子材料有限公司 | 一种混杂型光敏树脂及其制备方法 |
| CN111925741B (zh) * | 2016-10-28 | 2021-11-09 | 苏州太湖电工新材料股份有限公司 | 一种单面玻璃布补强少胶云母带及线棒 |
| US11453743B2 (en) * | 2020-06-05 | 2022-09-27 | Chanda Chemical Corp. | Thermoset epoxy resin, its preparing composition and making process thereof |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE528443A (enExample) | 1953-04-29 | |||
| NL7000025A (enExample) | 1969-01-08 | 1970-07-10 | ||
| JPS55164254A (en) * | 1979-06-06 | 1980-12-20 | Dainippon Toryo Co Ltd | Modified epoxy coating composition |
| US4521490A (en) | 1983-08-11 | 1985-06-04 | Minnesota Mining And Manufacturing Co. | Two-part epoxy composition |
| US4816546A (en) | 1987-06-23 | 1989-03-28 | The Dow Chemical Company | Mixed epoxy resins comprising sulfide containing aliphatic epoxy resins |
| US5364914A (en) | 1988-10-05 | 1994-11-15 | Imperial Chemical Industries Plc | Moulding composition comprising a thermoset component and thermoplast component |
| AU602822B2 (en) | 1988-10-05 | 1990-10-25 | National Starch & Chemical Corporation | Self fixturing structural adhesives |
| US5225486A (en) * | 1989-08-31 | 1993-07-06 | Amoco Corporation | Epoxy resins containing epoxidized polybutenes |
| JPH04175376A (ja) * | 1990-11-08 | 1992-06-23 | Nippon Oil & Fats Co Ltd | 熱硬化性組成物 |
| US5405731A (en) * | 1992-12-22 | 1995-04-11 | E. I. Du Pont De Nemours And Company | Aqueous processable, multilayer, photoimageable permanent coatings for printed circuits |
| JPH07179564A (ja) * | 1993-12-24 | 1995-07-18 | Nippon Steel Chem Co Ltd | 低粘度結晶性エポキシ樹脂の製造方法 |
| US5993909A (en) | 1995-06-06 | 1999-11-30 | Nof Corporation | Thermosetting compositions, methods of coating and coated articles |
| US6180200B1 (en) * | 1998-06-01 | 2001-01-30 | Dsm N. V. | Cationic and hybrid radiation curable pressure sensitive adhesives for bonding of optical discs |
| JP2000026828A (ja) * | 1998-07-13 | 2000-01-25 | Sekisui Chem Co Ltd | 接着剤組成物 |
| JP2000303053A (ja) * | 1999-04-23 | 2000-10-31 | Sekisui Chem Co Ltd | 接着剤組成物 |
| JP2000303052A (ja) * | 1999-04-23 | 2000-10-31 | Sekisui Chem Co Ltd | 接着剤組成物 |
| KR100372211B1 (ko) | 1999-06-17 | 2003-02-14 | 헨켈 록타이트 코오포레이션 | 조절가능하게 분해가능한 열경화성 수지 조성물, 상기 조성물을 사용하여 반도체 칩과 회로판 사이를 밀봉 언더필링하는 방법, 및 상기 조성물을 사용하여 제조한 전자 장치 |
-
2001
- 2001-03-07 US US09/801,234 patent/US6800371B2/en not_active Expired - Lifetime
-
2002
- 2002-02-05 MX MXPA03007929A patent/MXPA03007929A/es active IP Right Grant
- 2002-02-05 AT AT02717397T patent/ATE301174T1/de not_active IP Right Cessation
- 2002-02-05 EP EP20020717397 patent/EP1366130B1/en not_active Expired - Lifetime
- 2002-02-05 KR KR1020037011642A patent/KR100933964B1/ko not_active Expired - Fee Related
- 2002-02-05 JP JP2002571782A patent/JP4481568B2/ja not_active Expired - Lifetime
- 2002-02-05 WO PCT/US2002/003471 patent/WO2002072725A1/en not_active Ceased
- 2002-02-05 DE DE2002605342 patent/DE60205342T2/de not_active Expired - Lifetime
- 2002-02-26 MY MYPI20020656A patent/MY128233A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR100933964B1 (ko) | 2009-12-28 |
| ATE301174T1 (de) | 2005-08-15 |
| JP2004532299A (ja) | 2004-10-21 |
| EP1366130B1 (en) | 2005-08-03 |
| DE60205342D1 (de) | 2005-09-08 |
| DE60205342T2 (de) | 2006-06-01 |
| MY128233A (en) | 2007-01-31 |
| KR20040030526A (ko) | 2004-04-09 |
| MXPA03007929A (es) | 2004-05-05 |
| EP1366130A1 (en) | 2003-12-03 |
| US6800371B2 (en) | 2004-10-05 |
| US20030017341A1 (en) | 2003-01-23 |
| WO2002072725A1 (en) | 2002-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6800371B2 (en) | Adhesives and adhesive compositions containing thioether groups | |
| CN103797083B (zh) | 柔软的双马来酰亚胺、苯并嗪、环氧酐加合物混合粘合剂 | |
| KR101329932B1 (ko) | 접착 조성물, 접착 필름 및 반도체 장치의 제조 방법 | |
| CN102786773A (zh) | 密封用薄片以及电子部件装置 | |
| CN113897163A (zh) | 一种粘接剂、芯片键合膜及其制备方法 | |
| CN106947257B (zh) | 环氧改性有机硅树脂、制造方法、固化性组合物和电子部件 | |
| CN1308376C (zh) | 新型含硫酚醛树脂、其制法、具有硫醚构造或二硫化物构造的酚衍生物、其制法及环氧树脂组合物及粘着剂 | |
| KR101475139B1 (ko) | 반도체 장치 제조용 마스크 시트 및 이를 이용한 반도체 장치의 제조 방법 | |
| KR20040044136A (ko) | 웨이퍼 다이싱 및 다이본드 시트 | |
| TW202219214A (zh) | 導電性單組分型(1k)環氧樹脂調配物 | |
| TW201840770A (zh) | 半導體裝置製造用接著片及使用其之半導體裝置之製造方法 | |
| KR100516161B1 (ko) | 실란 화합물, 그 제조방법 및 이를 사용한 유기 다이 붙임접착제와 무기물 사이의 결합방법 | |
| TWI647797B (zh) | Sealing material with semiconductor sealing substrate, semiconductor device, and method of manufacturing semiconductor device | |
| JP2010006912A (ja) | 接着剤組成物、接着フィルム及びダイシング・ダイアタッチフィルム | |
| JP5935339B2 (ja) | 電子機器用接着剤組成物 | |
| JP4235808B2 (ja) | 接着剤組成物及び接着フィルム | |
| JP2000017240A (ja) | 接着シートおよびそれを用いた半導体装置 | |
| JP2007246886A (ja) | 接着剤組成物、接着フィルム及び半導体装置の製造方法 | |
| JP2008095014A (ja) | Ｑｆｎ用熱硬化型樹脂組成物および接着シート | |
| JP4586966B2 (ja) | 接着剤組成物及び接着フィルム | |
| JP2020143237A (ja) | 接着剤組成物 | |
| JP2003012710A (ja) | 低誘電正接樹脂組成物、その硬化物ならびに該組成物を用いたプリプレグ、積層板及び多層プリント基板 | |
| JP2009158817A (ja) | Ｑｆｎ用熱硬化型樹脂組成物及びそれを用いたｑｆｎ用接着シート | |
| WO2007083673A1 (ja) | 液状エポキシ樹脂組成物及びこれを用いた接着剤 | |
| TWI851825B (zh) | 黏著劑組合物及黏著片 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050202 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050202 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080620 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080701 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080930 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20081007 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20081106 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091110 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100122 |
|
| 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: 20100216 |
|
| 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: 20100318 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130326 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130326 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140326 Year of fee payment: 4 |
|
| 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 |