JP2010260101A - 硬化剤組成物 - Google Patents
硬化剤組成物 Download PDFInfo
- Publication number
- JP2010260101A JP2010260101A JP2010088842A JP2010088842A JP2010260101A JP 2010260101 A JP2010260101 A JP 2010260101A JP 2010088842 A JP2010088842 A JP 2010088842A JP 2010088842 A JP2010088842 A JP 2010088842A JP 2010260101 A JP2010260101 A JP 2010260101A
- Authority
- JP
- Japan
- Prior art keywords
- curing agent
- agent composition
- mold
- ester compound
- dimethyl
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- -1 ester compound Chemical class 0.000 claims abstract description 92
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 53
- 239000005011 phenolic resin Substances 0.000 claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 9
- 239000004576 sand Substances 0.000 claims description 62
- 239000000178 monomer Substances 0.000 claims description 20
- 238000000465 moulding Methods 0.000 claims description 20
- 238000005266 casting Methods 0.000 claims description 16
- ZWKKRUNHAVNSFW-UHFFFAOYSA-N dimethyl 2-methylpentanedioate Chemical compound COC(=O)CCC(C)C(=O)OC ZWKKRUNHAVNSFW-UHFFFAOYSA-N 0.000 claims description 7
- RZZLQHQXWZLBCJ-UHFFFAOYSA-N dimethyl 2-ethylbutanedioate Chemical compound COC(=O)C(CC)CC(=O)OC RZZLQHQXWZLBCJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- STCNNBXPNILVDE-UHFFFAOYSA-N methyl 3-aminothieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(N)=C(C(=O)OC)SC2=N1 STCNNBXPNILVDE-UHFFFAOYSA-N 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- YXAGIRHBJJLWHW-UHFFFAOYSA-N Ethyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC YXAGIRHBJJLWHW-UHFFFAOYSA-N 0.000 claims description 2
- ITUVXOFRQNQOOB-UHFFFAOYSA-N diethyl 2-ethylpentanedioate Chemical compound CCOC(=O)CCC(CC)C(=O)OCC ITUVXOFRQNQOOB-UHFFFAOYSA-N 0.000 claims description 2
- REJWPELGCLGVRK-UHFFFAOYSA-N dimethyl 2-methyldecanedioate Chemical compound COC(=O)CCCCCCCC(C)C(=O)OC REJWPELGCLGVRK-UHFFFAOYSA-N 0.000 claims description 2
- KICUISADAVMYCJ-UHFFFAOYSA-N methyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC KICUISADAVMYCJ-UHFFFAOYSA-N 0.000 claims description 2
- LVGHOOBZAPGKIH-UHFFFAOYSA-N diethyl 2-methylheptanedioate Chemical compound CCOC(=O)CCCCC(C)C(=O)OCC LVGHOOBZAPGKIH-UHFFFAOYSA-N 0.000 claims 1
- 239000004848 polyfunctional curative Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000004898 kneading Methods 0.000 description 10
- 150000002895 organic esters Chemical class 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 7
- 150000002989 phenols Chemical class 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 229960001755 resorcinol Drugs 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-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
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OVOUKWFJRHALDD-UHFFFAOYSA-N 2-[2-(2-acetyloxyethoxy)ethoxy]ethyl acetate Chemical compound CC(=O)OCCOCCOCCOC(C)=O OVOUKWFJRHALDD-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 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
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 244000226021 Anacardium occidentale Species 0.000 description 1
- 229910001018 Cast iron Inorganic materials 0.000 description 1
- 229910001208 Crucible steel Inorganic materials 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- RLJPRFQENAIMSK-UHFFFAOYSA-N dimethyl 2-ethylnonanedioate Chemical compound COC(=O)C(CC)CCCCCCC(=O)OC RLJPRFQENAIMSK-UHFFFAOYSA-N 0.000 description 1
- DSXXWHUALMCBTK-UHFFFAOYSA-N dimethyl 2-methyloctanedioate Chemical compound COC(=O)CCCCCC(C)C(=O)OC DSXXWHUALMCBTK-UHFFFAOYSA-N 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 150000002485 inorganic esters Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 229910021652 non-ferrous alloy Inorganic materials 0.000 description 1
- 229910052609 olivine Inorganic materials 0.000 description 1
- 239000010450 olivine Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22C—FOUNDRY MOULDING
- B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
- B22C1/02—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by additives for special purposes, e.g. indicators, breakdown additives
- B22C1/10—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by additives for special purposes, e.g. indicators, breakdown additives for influencing the hardening tendency of the mould material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
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Abstract
【解決手段】本発明の硬化剤組成物は、鋳型の製造に用いられる水溶性フェノール樹脂用の硬化剤組成物であって、分岐鎖を有するカルボン酸とアルコールとから導かれる炭素数5〜13の分岐エステル化合物を含有する硬化剤組成物である。
【選択図】なし
Description
本発明の硬化剤組成物には、鋳型の最終強度を低下させることなく、可使時間を充分に確保するために、上述した分岐エステル化合物が含有される。この分岐エステル化合物の炭素数は5〜13であるが、可使時間を充分に確保するためには、炭素数が6以上であることが好ましく、7以上であることがより好ましい。また、鋳型強度の観点からは、炭素数が10以下であることが好ましい。以上の観点から、分岐エステル化合物の炭素数は、6〜13であることが好ましく、7〜10であることがより好ましい。
本発明の硬化剤組成物は、上述した分岐エステル化合物のみからなるものであっても良いが、上記本発明の効果を阻害しない程度に、硬化成分として他のエステル化合物が含有されてもよい。このような他のエステル化合物としては、分子内にエステル結合を1〜5個有するエステル化合物が挙げられ、例えば、環状エステル化合物、直鎖構造のカルボン酸とアルコールとから導かれるエステル化合物、及び無機エステルから選ばれる1種以上のエステル化合物が挙げられる。具体的には、γ−ブチロラクトン、プロピオンラクトン、ε−カプロラクトン、ギ酸エチル、エチレングリコールジアセテート、ジエチレングリコールジアセテート、トリエチレングリコールジアセテート、エチレングリコールモノアセテート、トリアセチン、アセト酢酸エチル、コハク酸ジメチル、グルタル酸ジメチル、アジピン酸ジメチル等の有機エステルや、炭酸エチレン、炭酸プロピレン等の無機エステルや、これらの混合物等が例示できる。
本発明の硬化剤組成物には、フェノール化合物単量体が含有されてもよい。外気温度が高い場合(例えば40℃以上の場合)においても、鋳型の最終強度を低下させることなく、可使時間を延長できるからである。本発明の硬化剤組成物にフェノール化合物単量体を含有させた場合に、鋳型の最終強度を低下させることなく、可使時間を延長させ得る理由は、次の如く推定される。即ち、フェノール化合物単量体と分岐エステル化合物を共存させることにより、エステルの加水分解による水溶性フェノール樹脂の活性化及び高分子化が遅延され可使時間が延び、更に、活性化されたフェノール化合物単量体が水溶性フェノール樹脂中に組込まれることから、鋳型の最終強度が低下しないものと考えられる。また、これらの好ましい効果は、硬化剤組成物と水溶性フェノール樹脂と鋳物砂の混合物の温度が比較的高い場合、即ち30℃以上の場合に顕著であり、更に40℃以上、より更に45℃以上である場合に顕著となる。
本発明の硬化剤組成物には、混練砂の流動性を向上させるために、炭素数1〜8のアルキル基を有するアルキルシリケート又はその低縮合物(縮合度1〜10)を添加してもよい。前記アルキルシリケート又はその低縮合物の添加量は、分岐エステル化合物を含むエステル化合物100重量部に対して、2〜20重量部が好ましく、3〜15重量部がより好ましい。その他にも、本発明の効果を阻害しない程度に香料や界面活性剤等の添加剤を添加してもよい。これら添加剤の添加量は、分岐エステル化合物を含むエステル化合物100重量部に対して、0.001〜20重量部が好ましい。
(a)サンプル調製:試料に同重量のイオン交換水を加え、0.1重量%のH2SO4を加えて中和する。生成した沈殿を濾過分離し、水洗し、乾燥する。これをテトラヒドロフラン(THF)に溶解し、GPC用のサンプルを調製する。
(b)カラム:ガードカラムTSX(東洋曹達工業社製)HXL(6.5mmφ×4cm)1本と、TSK3000HXL(7.8mmφ×30cm)1本と、TSK2500HXL(7.8mmφ×30cm)1本を使用する。注入口側よりガードカラム−3000HXL−2500HXLの順に接続する。
(c)標準物質:ポリスチレン(東洋曹達工業社製)
(d)溶出液:THF(流速:1cm3/min)
(e)カラム温度:25℃
(f)検出器:紫外分光光度計(フェノールの紫外吸収の最大ピークの波長において定量)
(g)分子量計算の為の分割法:時間分割(2sec)
Claims (6)
- 鋳型の製造に用いられる水溶性フェノール樹脂用の硬化剤組成物であって、
分岐鎖を有するカルボン酸とアルコールとから導かれる炭素数5〜13の分岐エステル化合物を含有する、硬化剤組成物。 - 前記分岐エステル化合物が2−エチルコハク酸ジメチル、2−メチルグルタル酸ジメチル、2−メチルアジピン酸ジメチル、2−エチルヘキサン酸メチル、2−エチルヘキサン酸エチル、2−メチルセバシン酸ジメチル、2−エチルアゼライン酸ジメチル、2−エチルグルタル酸ジエチル、2−(n−プロピル)グルタル酸ジメチル、2−(n−ブチル)コハク酸ジエチル、2−(n−ブチル)コハク酸ジメチル、2−メチルピメリン酸ジエチル及び2−メチルスベリン酸ジメチルから選ばれる1種以上である請求項1記載の硬化剤組成物。
- 更にフェノール化合物単量体を含有する請求項1又は2記載の硬化剤組成物。
- 更に他のエステル化合物を含有する請求項1〜3の何れか1項記載の硬化剤組成物。
- 前記分岐エステル化合物と前記他のエステル化合物との重量比(分岐エステル化合物/他のエステル化合物)が、1/99〜99/1である請求項4記載の硬化剤組成物。
- 鋳物砂に硬化剤組成物及び水溶性フェノール樹脂を添加して得られた混合物を型込めして造型する鋳型の製造方法であって、
前記硬化剤組成物が請求項1〜5の何れか1項記載の硬化剤組成物であり、型込めする際の前記混合物の温度が30℃以上である、鋳型の製造方法。
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WO2013082266A1 (en) * | 2011-12-01 | 2013-06-06 | Rhodia Operations | Systems and methods for dispersing graphitic carbon |
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US20170174814A1 (en) * | 2015-12-18 | 2017-06-22 | Ha-International, Llc | Compositions and Methods for Modified Ester-Curatives and Reduction of Formaldehyde Emission and Odor in Ester-Cured Phenolic Binder Systems |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05200481A (ja) * | 1992-01-30 | 1993-08-10 | Kao Corp | 有機エステル硬化型鋳物砂用粘結剤組成物及びこれを用いた鋳型の製造方法 |
JPH07308732A (ja) * | 1994-05-16 | 1995-11-28 | Hodogaya Ashland Kk | 鋳型製造用粘結剤、及びそれを使用した鋳造用鋳型の製造方法 |
JPH08164439A (ja) * | 1994-12-14 | 1996-06-25 | Asahi Organic Chem Ind Co Ltd | 樹脂被覆骨材 |
JP2003511518A (ja) * | 1999-10-12 | 2003-03-25 | ボーデン・ケミカル・インコーポレーテッド | エステル硬化結合剤の改良 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5096983A (en) * | 1990-08-02 | 1992-03-17 | Borden, Inc. | Method for making a phenolic resole resin composition having extended work life |
US5214079A (en) * | 1990-08-02 | 1993-05-25 | Borden, Inc. | Accelerators for curing phenolic resole resins |
JP2542144B2 (ja) | 1992-01-30 | 1996-10-09 | 花王株式会社 | 有機エステル硬化型鋳物砂用粘結剤組成物及びこれを用いた鋳型の製造方法 |
JPH09104803A (ja) | 1995-08-08 | 1997-04-22 | Nippon Paint Co Ltd | 硬化性樹脂組成物、塗料組成物および塗膜形成方法 |
CA2182761A1 (en) | 1995-08-08 | 1997-02-09 | Manabu Yoshioka | Curable resin composition, coating composition and method for forming coated film |
JP3215945B2 (ja) | 1997-07-14 | 2001-10-09 | 群栄化学工業株式会社 | 鋳物砂用のエステル硬化型硬化剤組成物 |
JP4372535B2 (ja) | 2003-12-25 | 2009-11-25 | 旭有機材工業株式会社 | 鋳型用粘結剤組成物及びそれを用いてなる自硬性鋳型、並びに自硬性鋳型の製造方法 |
US7986623B2 (en) * | 2006-10-16 | 2011-07-26 | Fujitsu Limited | System and method for rejecting a request to alter a connection |
-
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05200481A (ja) * | 1992-01-30 | 1993-08-10 | Kao Corp | 有機エステル硬化型鋳物砂用粘結剤組成物及びこれを用いた鋳型の製造方法 |
JPH07308732A (ja) * | 1994-05-16 | 1995-11-28 | Hodogaya Ashland Kk | 鋳型製造用粘結剤、及びそれを使用した鋳造用鋳型の製造方法 |
JPH08164439A (ja) * | 1994-12-14 | 1996-06-25 | Asahi Organic Chem Ind Co Ltd | 樹脂被覆骨材 |
JP2003511518A (ja) * | 1999-10-12 | 2003-03-25 | ボーデン・ケミカル・インコーポレーテッド | エステル硬化結合剤の改良 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |