JPWO2016158175A1 - バインダー樹脂組成物 - Google Patents
バインダー樹脂組成物 Download PDFInfo
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- JPWO2016158175A1 JPWO2016158175A1 JP2017509430A JP2017509430A JPWO2016158175A1 JP WO2016158175 A1 JPWO2016158175 A1 JP WO2016158175A1 JP 2017509430 A JP2017509430 A JP 2017509430A JP 2017509430 A JP2017509430 A JP 2017509430A JP WO2016158175 A1 JPWO2016158175 A1 JP WO2016158175A1
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- JP
- Japan
- Prior art keywords
- group
- formula
- resin composition
- aliphatic polycarbonate
- binder resin
- 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
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- 239000011230 binding agent Substances 0.000 title claims abstract description 54
- 239000011342 resin composition Substances 0.000 title claims abstract description 48
- -1 lost foam casting Substances 0.000 claims abstract description 74
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 44
- 239000004431 polycarbonate resin Substances 0.000 claims abstract description 44
- 229920005668 polycarbonate resin Polymers 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 125000004185 ester group Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical group [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004036 acetal group Chemical group 0.000 claims abstract description 5
- 125000001033 ether group Chemical group 0.000 claims abstract description 5
- 229920000379 polypropylene carbonate Polymers 0.000 claims description 23
- 239000010419 fine particle Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000654 additive Substances 0.000 abstract description 9
- 230000000996 additive effect Effects 0.000 abstract description 6
- 229920006167 biodegradable resin Polymers 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 230000003287 optical effect Effects 0.000 abstract description 4
- 239000002775 capsule Substances 0.000 abstract description 2
- 229910010293 ceramic material Inorganic materials 0.000 abstract description 2
- 239000000835 fiber Substances 0.000 abstract description 2
- 239000010408 film Substances 0.000 abstract description 2
- 238000010114 lost-foam casting Methods 0.000 abstract description 2
- 239000012567 medical material Substances 0.000 abstract description 2
- 239000013307 optical fiber Substances 0.000 abstract description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 48
- 239000011347 resin Substances 0.000 description 48
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 30
- 238000004519 manufacturing process Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000000354 decomposition reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000001569 carbon dioxide Substances 0.000 description 15
- 229910002092 carbon dioxide Inorganic materials 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 14
- 238000005979 thermal decomposition reaction Methods 0.000 description 12
- 229910004298 SiO 2 Inorganic materials 0.000 description 11
- 238000005245 sintering Methods 0.000 description 11
- 229910052725 zinc Inorganic materials 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- 150000002118 epoxides Chemical class 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000004898 kneading Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000919 ceramic Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 229940014800 succinic anhydride Drugs 0.000 description 6
- 229910015902 Bi 2 O 3 Inorganic materials 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920001748 polybutylene Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 239000001716 (4-methyl-1-propan-2-yl-1-cyclohex-2-enyl) acetate Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 229910007472 ZnO—B2O3—SiO2 Inorganic materials 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- UODXCYZDMHPIJE-UHFFFAOYSA-N menthanol Chemical compound CC1CCC(C(C)(C)O)CC1 UODXCYZDMHPIJE-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 229940116411 terpineol Drugs 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003752 zinc compounds Chemical class 0.000 description 2
- DEUGOISHWHDTIR-UHFFFAOYSA-N (1-hydroxy-5,5-dimethylhexyl) 2-methylpropanoate Chemical compound C(C(C)C)(=O)OC(CCCC(C)(C)C)O DEUGOISHWHDTIR-UHFFFAOYSA-N 0.000 description 1
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- AACMXYCXYZGNBT-UHFFFAOYSA-N trimethyl(oxiran-2-ylmethoxy)silane Chemical compound C[Si](C)(C)OCC1CO1 AACMXYCXYZGNBT-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
しかし、焼結の際の高温条件下において酸素が存在すると、無機成分が変質してしまい、焼結体の性能が低下する場合があり、焼結後に、還元雰囲気下でさらに焼結する工程が必要となることが多い。従って、焼結の際に酸素を供給せずに消失することができるバインダーが望まれている。
さらに、前述のバインダーは、発熱分解するため、焼結炉内の温度を制御しながら、一度に大量に焼結することが困難である。
〔1〕 式(1):
で表される脂肪族ポリカーボネート樹脂と、式(2):
で表される末端封止脂肪族ポリカーボネート樹脂を含む、バインダー樹脂組成物、並びに
〔2〕 前記〔1〕記載のバインダー樹脂組成物、無機微粒子、及び溶媒を含有する、無機微粒子分散ペースト組成物
に関する。
で表される脂肪族ポリカーボネート樹脂と、式(2):
で表される末端封止脂肪族ポリカーボネート樹脂を含む。通常、2種類の樹脂を混合し熱分解させると、それぞれの樹脂が独立して熱分解をするが、本発明のバインダー樹脂組成物は、それぞれの樹脂の混合比率に応じ、あたかも単一の樹脂の熱分解のごとく分解するため、バインダー樹脂組成物の分解温度を精度良く制御することができる。
ゲルパーミエーションクロマトグラフィー(日本ウォーターズ製、Waters 2695 セパレーションモジュール)を用いて、30mmol/LのN,N-ジメチルホルミアミド臭化リチウム溶液中40℃にて測定し、標準ポリスチレンを基準にして、質量平均分子量(Mw)及び数平均分子量(Mn)を算出し、分子量分布(Mw/Mn)を求めた。
攪拌機、窒素ガス導入管、温度計、ディーンスターク管、及び還流冷却管を備えた1L容の四つ口フラスコに、酸化亜鉛77.3g(0.95mol)、グルタル酸123g(1mol)、酢酸1.14g(0.02mol)及びトルエン760gを仕込んだ。次に、反応系内に50mL/minの流量で窒素を流しながら、55℃まで昇温し、同温度で4時間攪拌して反応させた。その後、110℃まで昇温し、さらに同温度で2時間攪拌して共沸脱水させ、水分を除去した後、室温まで冷却して、有機亜鉛触媒を含むスラリー液を得た。
攪拌機、ガス導入管、及び温度計を備えた1L容のオートクレーブの系内をあらかじめ窒素雰囲気に置換した後、触媒製造例1により得られた有機亜鉛触媒を含むスラリー液117.3g(有機亜鉛触媒を135mmol含む)、炭酸ジメチル577.2g、及びプロピレンオキシド78.3g(1.35mol)を仕込んだ。次に、攪拌下、二酸化炭素を加え、反応系内が1MPaとなるまで二酸化炭素を充填した。その後、60℃に昇温し、反応により消費される二酸化炭素を補給しながら8時間重合反応を行った。二酸化炭素の消費量は、1.17molであった。反応終了後、オートクレーブを冷却して脱圧したところに、無水コハク酸0.7g(全てのモノマーが反応したと仮定した場合の樹脂100質量部に対して0.5質量部)を添加し、40℃で1時間攪拌した。反応溶液をろ過した後、減圧乾燥して、無水コハク酸により末端がカルボキシ基で封止されたポリプロピレンカーボネート樹脂(A)120gを得た。得られたポリプロピレンカーボネートの質量平均分子量(Mw)は236,000、分子量分布(Mw/Mn)は10.0であった。
反応終了後、オートクレーブを冷却して脱圧した後、無水コハク酸を添加せず、反応溶液をろ過し、減圧乾燥した以外は、樹脂製造例1と同様にして、ポリプロピレンカーボネート樹脂(B)123gを得た。得られたポリプロピレンカーボネートの質量平均分子量は315,000、分子量分布(Mw/Mn)は9.74であった
ポリプロピレンカーボネート樹脂(B)40gと4,4’-ジフェニルメタンジイソシアネート0.4gを混練機(東洋精機製作所製、ラボプラストミル4C150)に投入し、混練温度160℃、回転数40r/minで5分間、溶融混練を行い、末端がイソシアネート基で封止されたポリプロピレンカーボネート樹脂(C)を得た。得られたポリプロピレンカーボネートの質量平均分子量は323,000、分子量分布(Mw/Mn)は8.82であった。
ポリエチレンカーボネート樹脂(D)(Empowermaterials社製、商品名QPAC25、Mw:198,000、Mw/Mn:3.48)40gとコハク酸無水物0.3gを混練機(東洋精機製作所製、ラボプラストミル4C150)に投入し、混練温度100℃、回転数40r/minで5分間、溶融混練を行い、無水コハク酸により末端がカルボキシ基で封止されたポリエチレンカーボネート樹脂(E)を得た。得られたポリエチレンカーボネートの質量平均分子量は197,000、分子量分布(Mw/Mn)は3.49であった。
攪拌機、ガス導入管、及び温度計を備えた1L容のオートクレーブの系内をあらかじめ窒素雰囲気に置換した後、触媒製造例1により得られた有機亜鉛触媒を含むスラリー液117.3g(有機亜鉛触媒を135mmol含む)、炭酸ジメチル577.2g、及び1,2-ブチレンオキシド97.3g(1.35mol)を仕込んだ。次に、攪拌下、二酸化炭素を加え、反応系内が1MPaとなるまで二酸化炭素を充填した。その後、60℃に昇温し、反応により消費される二酸化炭素を補給しながら8時間重合反応を行った。二酸化炭素の消費量は、1.02molであった。反応終了後、オートクレーブを冷却して脱圧し、ろ過した後、減圧乾燥してポリブチレンカーボネート樹脂(F)118gを得た。得られたポリブチレンカーボネートの質量平均分子量は273,000、分子量分布(Mw/Mn)は12.2であった。
樹脂製造例5で得られたポリブチレンカーボネート樹脂(F)11.6g(100mmol)をジクロロメタン120gに溶解させ、無水酢酸0.51g(5.0mmol)、トリエチルアミン0.3g(3.25mmol)及び4,4-ジメチルアミノピリジン0.2g(1.63mmol)を加え、25℃で24時間攪拌した。揮発分を除去し、残留物をメタノール200mLに注ぎ、析出した白色ポリマーを乾燥することで、無水酢酸により末端がエステル基で封止されたポリブチレンカーボネート樹脂(G)を得た。得られたポリブチレンカーボネートの質量平均分子量は290,000、分子量分布(Mw/Mn)は10.4であった。
50mL容ガラスバイアルに樹脂製造例1で得られたポリプロピレンカーボネート樹脂(A)0.2gと樹脂製造例2で得られたポリプロピレンカーボネート樹脂(B)0.8gを計りとり、アセトン10gに溶解させ、均一な溶液を調製した。この溶液を乾燥させ、バインダー樹脂組成物1.0gを得た。得られたバインダー樹脂組成物の熱分解開始温度は215.5℃、50質量%分解温度は217.2℃であった。
ポリプロピレンカーボネート樹脂(A)とポリプロピレンカーボネート樹脂(B)とを、表1に記載の比率で使用した以外は、実施例1と同様にして、バインダー樹脂組成物1.0gを得た。
ポリプロピレンカーボネート樹脂(A)又はポリプロピレンカーボネート樹脂(B)1.0gをアセトン10gに溶解させ、均一な溶液を調製した。この溶液を乾燥させ、バインダー樹脂組成物1.0gを得た。
エスアイアイ・ナノテクノロジー社製TG/DTA7220を用い、窒素雰囲気下、10℃/minの昇温速度で室温から500℃まで昇温しながら、熱重量の変化を測定する。熱分解開始温度(Td)は、試験加熱開始前の質量を通る横軸に平行な線と、分解曲線における屈曲点間の勾配が最大となるように引いた接線との交点とする。50質量%分解温度(Td50)は、サンプルの熱質量が試験加熱開始前の質量の半分(50%)になったときの温度を読み取る。
ポリプロピレンカーボネート樹脂(B)とポリプロピレンカーボネート樹脂(C)とを、表2に記載の比率で使用した以外は、実施例1と同様にして、バインダー樹脂組成物1.0gを得た。
ポリプロピレンカーボネート樹脂(C)1.0gをアセトン10gに溶解させ、均一な溶液を調製した。この溶液を乾燥させ、バインダー樹脂組成物1.0gを得た。
ポリエチレンカーボネート樹脂(D)とポリエチレンカーボネート樹脂(E)とを、表3に記載の比率で使用した以外は、実施例1と同様にして、バインダー樹脂組成物1.0gを得た。
ポリエチレンカーボネート樹脂(D)又はポリエチレンカーボネート樹脂(E)1.0gをアセトン10gに溶解させ、均一な溶液を調製した。この溶液を乾燥させ、バインダー樹脂組成物1.0gを得た。
ポリブチレンカーボネート樹脂(F)とポリブチレンカーボネート樹脂(G)とを、表4に記載の比率で使用した以外は、実施例1と同様にして、バインダー樹脂組成物1.0gを得た。
ポリブチレンカーボネート樹脂(F)又はポリブチレンカーボネート樹脂(G)1.0gをアセトン10gに溶解させ、均一な溶液を調製した。この溶液を乾燥させ、バインダー樹脂組成物1.0gを得た。
無機微粒子分散ペーストの製造例
10mL容のガラスバイアルに実施例1で得られたバインダー樹脂組成物0.12gを量りとり、N-メチル-2-ピロリドン0.88gに溶解させ、均一な溶液を調製する。乳鉢に銀粒子4.0gを量りとり、調整した溶液を加えながら、滑らかになるまで20分間混錬し、銀粒子分散ペースト5.0gを得る。
10mL容のガラスバイアルに実施例1で得られたバインダー樹脂組成物0.12gを量りとり、N-メチル-2-ピロリドン0.88gに溶解させ、均一な溶液を調製する。この溶液全量と、アルミナ粒子4.0gを混合し、自転公転ミキサーを用いて混錬してペースト化した後、さらに3本ロールミルを用いて混錬し、アルミナ分散ペースト5.0gを得る。
Claims (4)
- 式(1):
で表される脂肪族ポリカーボネート樹脂と、式(2):
で表される末端封止脂肪族ポリカーボネート樹脂を含む、バインダー樹脂組成物。 - 式(2)において、X及びYが、カルボキシ基、エステル基、カルバメート基及びイソシアネート基から選ばれる少なくとも1種の官能基を末端に有する基である、請求項1記載のバインダー樹脂組成物。
- 式(1)で表される脂肪族ポリカーボネート樹脂及び/又は式(2)で表される脂肪族ポリカーボネート樹脂が、ポリエチレンカーボネート、ポリプロピレンカーボネート及びポリブチレンカーボネートからなる群より選ばれる少なくとも1種である、請求項1又は2記載のバインダー樹脂組成物。
- 請求項1〜3いずれか記載のバインダー樹脂組成物、無機微粒子、及び溶媒を含有する、無機微粒子分散ペースト組成物。
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JP2015068377 | 2015-03-30 | ||
PCT/JP2016/056412 WO2016158175A1 (ja) | 2015-03-30 | 2016-03-02 | バインダー樹脂組成物 |
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WO2012128028A1 (ja) * | 2011-03-18 | 2012-09-27 | 住友精化株式会社 | 金属ペースト組成物 |
JP2012224675A (ja) * | 2011-04-15 | 2012-11-15 | Sumitomo Seika Chem Co Ltd | ポリカーボネート樹脂組成物 |
JP2014501316A (ja) * | 2010-12-28 | 2014-01-20 | エスケー イノベーション カンパニー リミテッド | 熱安定性が改善されたポリプロピレンカーボネート樹脂の製造方法 |
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US406663A (en) * | 1889-07-09 | Gardener s and cotton-picker s brace | ||
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JPH06334282A (ja) * | 1993-05-24 | 1994-12-02 | Matsushita Electric Ind Co Ltd | セラミック多層基板用グリーンシート |
US8222347B2 (en) | 2007-07-25 | 2012-07-17 | Sabic Innovative Plastics Ip B.V. | Polyester-polycarbonate compositions |
JP6301146B2 (ja) * | 2014-02-06 | 2018-03-28 | 住友精化株式会社 | 脂肪族ポリカーボネート樹脂組成物及びそれを用いた成形体 |
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JPS62246856A (ja) * | 1986-04-19 | 1987-10-28 | 鐘淵化学工業株式会社 | セラミツクスの製造方法 |
JPH07224219A (ja) * | 1994-02-07 | 1995-08-22 | Mitsubishi Gas Chem Co Inc | ポリカーボネート樹脂組成物 |
JP2014501316A (ja) * | 2010-12-28 | 2014-01-20 | エスケー イノベーション カンパニー リミテッド | 熱安定性が改善されたポリプロピレンカーボネート樹脂の製造方法 |
WO2012128028A1 (ja) * | 2011-03-18 | 2012-09-27 | 住友精化株式会社 | 金属ペースト組成物 |
JP2012224675A (ja) * | 2011-04-15 | 2012-11-15 | Sumitomo Seika Chem Co Ltd | ポリカーボネート樹脂組成物 |
WO2015019771A1 (ja) * | 2013-08-09 | 2015-02-12 | 国立大学法人北陸先端科学技術大学院大学 | 酸化物半導体層及びその製造方法、並びに酸化物半導体の前駆体、酸化物半導体層、半導体素子、及び電子デバイス |
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PH12017501777A1 (en) | 2018-03-19 |
EP3279265B1 (en) | 2019-06-12 |
EP3279265A1 (en) | 2018-02-07 |
US20180057415A1 (en) | 2018-03-01 |
KR20170133402A (ko) | 2017-12-05 |
SG11201707442VA (en) | 2017-10-30 |
JP6745792B2 (ja) | 2020-08-26 |
TW201700604A (zh) | 2017-01-01 |
US10457607B2 (en) | 2019-10-29 |
EP3279265A4 (en) | 2018-09-05 |
CN107406669A (zh) | 2017-11-28 |
WO2016158175A1 (ja) | 2016-10-06 |
TWI683853B (zh) | 2020-02-01 |
CN107406669B (zh) | 2019-07-19 |
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