JPH0372098B2 - - Google Patents

Info

Publication number: JPH0372098B2
Authority: JP; Japan
Prior art keywords: resin; mixture; epoxy; resins; peroxide
Prior art date: 1982-08-05
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

Application number

JP61487A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62246936A (ja

Inventor

Dee Utsudoson Uein

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ashland LLC

Original Assignee

Ashland Oil Inc

Priority date (The priority date 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 date listed.)

1982-08-05

Filing date

1987-01-07

Publication date

1991-11-15

1987-01-07 Application filed by Ashland Oil Inc filed Critical Ashland Oil Inc

1987-10-28 Publication of JPS62246936A publication Critical patent/JPS62246936A/ja

1991-11-15 Publication of JPH0372098B2 publication Critical patent/JPH0372098B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 claims description 153
239000003822 epoxy resin Substances 0.000 claims description 120
229920000647 polyepoxide Polymers 0.000 claims description 120
229920005989 resin Polymers 0.000 claims description 113
239000011347 resin Substances 0.000 claims description 113
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 82
239000004576 sand Substances 0.000 claims description 57
238000000034 method Methods 0.000 claims description 56
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 48
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 41
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 claims description 40
150000002978 peroxides Chemical class 0.000 claims description 35
238000004519 manufacturing process Methods 0.000 claims description 22
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 22
229920003986 novolac Polymers 0.000 claims description 20
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 18
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 17
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 16
238000000465 moulding Methods 0.000 claims description 14
150000001451 organic peroxides Chemical class 0.000 claims description 13
239000000178 monomer Substances 0.000 claims description 12
229920001568 phenolic resin Polymers 0.000 claims description 12
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 9
239000000945 filler Substances 0.000 claims description 9
229920001187 thermosetting polymer Polymers 0.000 claims description 9
229910003480 inorganic solid Inorganic materials 0.000 claims description 7
239000002245 particle Substances 0.000 claims description 7
229920001807 Urea-formaldehyde Polymers 0.000 claims description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
229920000368 omega-hydroxypoly(furan-2,5-diylmethylene) polymer Polymers 0.000 claims description 5
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical group CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 claims description 3
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 3
229920002803 thermoplastic polyurethane Polymers 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 claims description 2
239000011261 inert gas Substances 0.000 claims 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 claims 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 76
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
238000001723 curing Methods 0.000 description 44
239000004593 Epoxy Substances 0.000 description 37
238000012360 testing method Methods 0.000 description 36
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 35
239000000047 product Substances 0.000 description 35
239000007789 gas Substances 0.000 description 31
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 25
-1 hydrogen halides Chemical class 0.000 description 22
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 20
229910000077 silane Inorganic materials 0.000 description 20
239000007800 oxidant agent Substances 0.000 description 18
239000003795 chemical substances by application Substances 0.000 description 17
239000002253 acid Substances 0.000 description 15
239000000463 material Substances 0.000 description 15
239000003054 catalyst Substances 0.000 description 14
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 12
238000009833 condensation Methods 0.000 description 10
230000005494 condensation Effects 0.000 description 10
238000010926 purge Methods 0.000 description 10
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
239000011230 binding agent Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000007849 furan resin Substances 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000011236 particulate material Substances 0.000 description 8
239000005011 phenolic resin Substances 0.000 description 8
230000008569 process Effects 0.000 description 8
239000007787 solid Substances 0.000 description 8
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 7
230000008901 benefit Effects 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001252 acrylic acid derivatives Chemical class 0.000 description 6
229940106691 bisphenol a Drugs 0.000 description 6
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
150000002432 hydroperoxides Chemical class 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
239000007822 coupling agent Substances 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
125000003700 epoxy group Chemical group 0.000 description 5
238000009472 formulation Methods 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000004844 aliphatic epoxy resin Substances 0.000 description 4
239000012159 carrier gas Substances 0.000 description 4
238000006482 condensation reaction Methods 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
RUGWIVARLJMKDM-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxymethyl)furan Chemical compound C1OC1COCC1=CC=CO1 RUGWIVARLJMKDM-UHFFFAOYSA-N 0.000 description 3
239000004925 Acrylic resin Substances 0.000 description 3
229920000178 Acrylic resin Polymers 0.000 description 3
229910015900 BF3 Inorganic materials 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
235000015895 biscuits Nutrition 0.000 description 3
238000005266 casting Methods 0.000 description 3
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000010408 film Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
238000012986 modification Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
239000003607 modifier Substances 0.000 description 3
239000011342 resin composition Substances 0.000 description 3
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
229920013683 Celanese Polymers 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
239000004115 Sodium Silicate Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000011353 cycloaliphatic epoxy resin Substances 0.000 description 2
238000006704 dehydrohalogenation reaction Methods 0.000 description 2
WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
239000003999 initiator Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
229920003987 resole Polymers 0.000 description 2
150000004756 silanes Chemical class 0.000 description 2
229910010271 silicon carbide Inorganic materials 0.000 description 2
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
229910052911 sodium silicate Inorganic materials 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
ZWUBFMWIQJSEQS-UHFFFAOYSA-N 1,1-bis(ethenyl)cyclohexane Chemical compound C=CC1(C=C)CCCCC1 ZWUBFMWIQJSEQS-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
NKWKILGNDJEIOC-UHFFFAOYSA-N 2-(2-chloroethyl)oxirane Chemical compound ClCCC1CO1 NKWKILGNDJEIOC-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
FKXQQICCTODPGY-UHFFFAOYSA-N 2-(3-chloropropyl)oxetane Chemical compound ClCCCC1CCO1 FKXQQICCTODPGY-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
239000004157 Nitrosyl chloride Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000006087 Silane Coupling Agent Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
239000003082 abrasive agent Substances 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
239000004841 bisphenol A epoxy resin Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KNMKGOLZNOKQGK-UHFFFAOYSA-N bromoborane Chemical compound BrB KNMKGOLZNOKQGK-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZGNIYAPHJAPRMA-UHFFFAOYSA-N chlorine azide Chemical compound ClN=[N+]=[N-] ZGNIYAPHJAPRMA-UHFFFAOYSA-N 0.000 description 1
125000004965 chloroalkyl group Chemical group 0.000 description 1
UOALEFQKAOQICC-UHFFFAOYSA-N chloroborane Chemical compound ClB UOALEFQKAOQICC-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
230000007547 defect Effects 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
239000012933 diacyl peroxide Substances 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229910001651 emery Inorganic materials 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
239000002223 garnet Substances 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000012784 inorganic fiber Substances 0.000 description 1
238000005495 investment casting Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000005058 metal casting Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
BMNDJWSIKZECMH-UHFFFAOYSA-N nitrosyl bromide Chemical compound BrN=O BMNDJWSIKZECMH-UHFFFAOYSA-N 0.000 description 1
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
235000019392 nitrosyl chloride Nutrition 0.000 description 1
ZEIYBPGWHWECHV-UHFFFAOYSA-N nitrosyl fluoride Chemical compound FN=O ZEIYBPGWHWECHV-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000012255 powdered metal Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011819 refractory material Substances 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000010112 shell-mould casting Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
UWRZIZXBOLBCON-UHFFFAOYSA-N styrylamine group Chemical group C(=CC1=CC=CC=C1)N UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000009864 tensile test Methods 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)
Epoxy Resins (AREA)
Processes Of Treating Macromolecular Substances (AREA)

JP61487A 1982-08-05 1987-01-07 成形充填体の製造方法 Granted JPS62246936A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US40542082A	1982-08-05	1982-08-05
US405420		1982-08-05
US436031		1982-10-22

Publications (2)

Publication Number	Publication Date
JPS62246936A JPS62246936A (ja)	1987-10-28
JPH0372098B2 true JPH0372098B2 (fr)	1991-11-15

Family

ID=23603629

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP14266983A Granted JPS5947225A (ja)	1982-08-05	1983-08-05	硬化性エポキシ樹脂組成物
JP61487A Granted JPS62246936A (ja)	1982-08-05	1987-01-07	成形充填体の製造方法

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
JP14266983A Granted JPS5947225A (ja)	1982-08-05	1983-08-05	硬化性エポキシ樹脂組成物

Country Status (2)

Country	Link
JP (2)	JPS5947225A (fr)
ZA (1)	ZA835532B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10227746B2 (en) *	2012-05-23	2019-03-12	Relborgn Pty Ltd	Method of limiting permeability of a matrix to limit liquid and gas inflow

1983
- 1983-07-28 ZA ZA835532A patent/ZA835532B/xx unknown
- 1983-08-05 JP JP14266983A patent/JPS5947225A/ja active Granted
1987
- 1987-01-07 JP JP61487A patent/JPS62246936A/ja active Granted

Also Published As

Publication number	Publication date
ZA835532B (en)	1984-09-26
JPS5947225A (ja)	1984-03-16
JPS62246936A (ja)	1987-10-28
JPS6340443B2 (fr)	1988-08-11

Publication	Publication Date	Title
US4518723A (en)	1985-05-21	Curable epoxy resin compositions and use in preparing formed, shaped, filled bodies
US3184814A (en)	1965-05-25	Process of forming a foundry mold with an acid curable binder
US4806576A (en)	1989-02-21	Curable epoxy resin compositions and use in preparing formed, shaped, filled bodies
US3639654A (en)	1972-02-01	Gaseous halo-sulfonic acid anhydride catalysts for curing furfuryl alcohols and furan resins
EP1474467B1 (fr)	2014-04-09	Liants de moulage en boite froide durcis a l'aide de radicaux libres et contenant un silicate d'alkyle
EP2046518B1 (fr)	2017-06-14	Procédé pour préparer des formes de fonderie résistant à l'érosion avec un liant de boite froide en epoxy-acrylate
JPH0788460B2 (ja)	1995-09-27	熱硬化性樹脂の常温硬化法
JPS5859929A (ja)	1983-04-09	シクロペンタジエン誘導体、その製造方法およびその誘導体を含む粘結剤組成物
JPH0372098B2 (fr)	1991-11-15
US4478962A (en)	1984-10-23	Binder compositions comprising furfuryl ester and furfuryl ester-furuyl alcohol combinations
US12303970B2 (en)	2025-05-20	Foundry mix including resorcinol
US4113916A (en)	1978-09-12	Shell sand with improved thermal shock resistance
JPS6096345A (ja)	1985-05-29	鋳型の製造方法
KR850001429B1 (ko)	1985-10-02	경화성 조성물
US20030066622A1 (en)	2003-04-10	Cold-box foundry binder systems
JPH0146219B2 (fr)	1989-10-06
JPS58500568A (ja)	1983-04-14	熱に安定なフエノ−ル樹脂成形物
KR20240007195A (ko)	2024-01-16	에스테르-경화된 페놀릭 본디드 주조 형상에서의 할로이사이트 튜브
JPH04371806A (ja)	1992-12-24	不燃性軽量樹脂複合体
JPH0417741B2 (fr)	1992-03-26
JPS6351996B2 (fr)	1988-10-17
JPS5961546A (ja)	1984-04-07	熱風硬化性鋳型粘結材料
JPS6317018B2 (fr)	1988-04-12
JPH06154939A (ja)	1994-06-03	鋳物砂用バインダーおよび鋳型の製造方法
JP2000051993A (ja)	2000-02-22	粘結剤組成物