CH621564A5 - - Google Patents
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- Publication number
- CH621564A5 CH621564A5 CH1002179A CH1002179A CH621564A5 CH 621564 A5 CH621564 A5 CH 621564A5 CH 1002179 A CH1002179 A CH 1002179A CH 1002179 A CH1002179 A CH 1002179A CH 621564 A5 CH621564 A5 CH 621564A5
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- acid
- epoxy resin
- carboxylic acid
- radical
- Prior art date
Links
- -1 hydrocarbon radicals Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 229920000647 polyepoxide Polymers 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000003822 epoxy resin Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 8
- 150000004714 phosphonium salts Chemical class 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229920013730 reactive polymer Polymers 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 description 19
- 239000002253 acid Substances 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
- 150000007513 acids Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 150000001735 carboxylic acids Chemical group 0.000 description 8
- 150000002118 epoxides Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
- 229940089960 chloroacetate Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 239000000178 monomer 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
- 230000000269 nucleophilic effect Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- 229940048053 acrylate Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000728 polyester Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
-
- 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
- C08G59/68—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 catalysts used
- C08G59/688—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 catalysts used containing phosphorus
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48159974A | 1974-06-21 | 1974-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621564A5 true CH621564A5 (xx) | 1981-02-13 |
Family
ID=23912608
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH809675A CH618198A5 (xx) | 1974-06-21 | 1975-06-20 | |
| CH810075A CH618449A5 (xx) | 1974-06-21 | 1975-06-20 | |
| CH809575A CH617944A5 (xx) | 1974-06-21 | 1975-06-20 | |
| CH1002179A CH621564A5 (xx) | 1974-06-21 | 1979-11-08 |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH809675A CH618198A5 (xx) | 1974-06-21 | 1975-06-20 | |
| CH810075A CH618449A5 (xx) | 1974-06-21 | 1975-06-20 | |
| CH809575A CH617944A5 (xx) | 1974-06-21 | 1975-06-20 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4132706A (xx) |
| JP (3) | JPS5119748A (xx) |
| BR (3) | BR7503896A (xx) |
| CA (3) | CA1041696A (xx) |
| CH (4) | CH618198A5 (xx) |
| DE (5) | DE2559587C3 (xx) |
| ES (2) | ES438785A1 (xx) |
| GB (3) | GB1492868A (xx) |
| ZA (3) | ZA753392B (xx) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5333599Y2 (xx) * | 1974-01-21 | 1978-08-18 | ||
| US4302574A (en) * | 1979-05-23 | 1981-11-24 | The Dow Chemical Company | Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids |
| USRE32951E (en) * | 1980-12-04 | 1989-06-13 | The Dow Chemical Company | Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts |
| US4370465A (en) * | 1980-12-04 | 1983-01-25 | The Dow Chemical Co. | Epoxy resins having improved physical properties when cured |
| US4410596A (en) * | 1980-12-04 | 1983-10-18 | The Dow Chemical Co. | Process for preparing epoxy resins having improved physical properties when cured |
| US4352918A (en) * | 1980-12-04 | 1982-10-05 | The Dow Chemical Company | Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts |
| DE3151540A1 (de) * | 1980-12-29 | 1982-08-19 | Ciba-Geigy GmbH, 7867 Wehr | "verwendung von transparenten anhydridhaertbaren epoxidgiessharzen" |
| US4389520A (en) * | 1982-04-05 | 1983-06-21 | Ciba-Geigy Corporation | Advancement catalysts for epoxy resins |
| US4496709A (en) * | 1982-06-23 | 1985-01-29 | The Dow Chemical Company | Process for preparing epoxy resins employing a phosphonium trifluoroacetate catalyst |
| WO1984000171A1 (en) * | 1982-06-23 | 1984-01-19 | Dow Chemical Co | Process for preparing advanced epoxy resins employing a phosphonium trifluoroacetate catalyst |
| US4465722A (en) * | 1982-07-08 | 1984-08-14 | Ciba-Geigy Corporation | Process for the preparation of epoxide resins by the advancement method |
| US4438254A (en) * | 1983-02-28 | 1984-03-20 | The Dow Chemical Company | Process for producing epoxy resins |
| US4477645A (en) * | 1983-07-21 | 1984-10-16 | The Dow Chemical Company | Immobilized epoxy advancement initiators |
| US4540823A (en) * | 1983-07-21 | 1985-09-10 | The Dow Chemical Company | Tetrahydrocarbyl phosphonium salts |
| JPS6053524A (ja) * | 1983-09-01 | 1985-03-27 | Asahi Chem Ind Co Ltd | 難燃性エポキシ樹脂組成物 |
| US4550154A (en) * | 1983-12-27 | 1985-10-29 | Ford Motor Company | Thermosetting coating composition |
| KR900000190B1 (ko) * | 1984-11-16 | 1990-01-23 | 미쓰비시전기 주식회사 | 에폭시수지 조성물 |
| AU594934B2 (en) * | 1984-12-04 | 1990-03-22 | Dow Chemical Company, The | Thermally stable thermoplastic resin |
| JPS61185528A (ja) * | 1985-02-12 | 1986-08-19 | Mitsubishi Electric Corp | エポキシ樹脂組成物 |
| US4634757A (en) * | 1985-07-15 | 1987-01-06 | Shell Oil Company | Fusion product |
| GB8523464D0 (en) * | 1985-09-23 | 1985-10-30 | Ici Plc | Insecticidal alkenes |
| US4732958A (en) * | 1986-12-30 | 1988-03-22 | Shell Oil Company | Epoxy fusion process |
| US5155196A (en) * | 1987-06-01 | 1992-10-13 | The Dow Chemical Company | Polymer resulting from the cure of a preformed chromene-containing mixture |
| JPH078973B2 (ja) * | 1987-11-27 | 1995-02-01 | 三井東圧化学株式会社 | 熱硬化性の溶剤型塗料組成物 |
| US4933420A (en) * | 1988-09-23 | 1990-06-12 | The Dow Chemical Company | Epoxy resins containing phosphonium catalysts |
| JP2547827B2 (ja) * | 1988-10-26 | 1996-10-23 | 昇 丸山 | 給湯システム |
| US4910329A (en) * | 1989-01-11 | 1990-03-20 | Rohm And Haas Company | Process for preparing hydroxyalkyl esters |
| US5310854A (en) * | 1989-08-23 | 1994-05-10 | The Dow Chemical Company | Epoxy resin composition and process therefor |
| US5164472A (en) * | 1990-01-18 | 1992-11-17 | The Dow Chemical Company | Hydroxy-functional polyethers as thermoplastic barrier resins |
| US4981926A (en) * | 1990-02-06 | 1991-01-01 | The Dow Chemical Company | Composition of epoxy resin, amino group-containing phosphonium catalyst and curing agent |
| US5208317A (en) * | 1990-02-06 | 1993-05-04 | The Dow Chemical Company | Composition comprising epoxy resin and cationic amine phosphonium catalyst |
| US5202407A (en) * | 1992-01-24 | 1993-04-13 | The Dow Chemical Company | Precatalyzed catalyst compositions, process for preparing epoxy resins curable compositions, articles resulting from curing the resultant compositions |
| US20020053734A1 (en) * | 1993-11-16 | 2002-05-09 | Formfactor, Inc. | Probe card assembly and kit, and methods of making same |
| US5414046A (en) * | 1994-06-17 | 1995-05-09 | General Electric Company | Flame retardant polymer compositions comprising thermally stable resins |
| KR100586763B1 (ko) * | 1998-07-02 | 2006-06-08 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 포스포늄보레이트 화합물, 그의 제조방법, 에폭시 수지 조성물용경화 촉매 및 에폭시 수지 조성물 |
| JP4373624B2 (ja) * | 2000-09-04 | 2009-11-25 | 富士フイルム株式会社 | 感熱性組成物、それを用いた平版印刷版原版及びスルホニウム塩化合物 |
| JP4569076B2 (ja) * | 2002-06-05 | 2010-10-27 | 住友ベークライト株式会社 | 硬化促進剤、エポキシ樹脂組成物および半導体装置 |
| JP4128420B2 (ja) * | 2002-09-27 | 2008-07-30 | 住友ベークライト株式会社 | エポキシ樹脂用硬化剤組成物、該硬化剤組成物を用いたエポキシ樹脂組成物および半導体装置 |
| US6855738B2 (en) | 2003-06-06 | 2005-02-15 | Dow Global Technologies Inc. | Nanoporous laminates |
| JP4496778B2 (ja) * | 2004-01-08 | 2010-07-07 | 住友ベークライト株式会社 | 硬化促進剤、エポキシ樹脂組成物および半導体装置 |
| JP5261880B2 (ja) * | 2006-02-27 | 2013-08-14 | 住友ベークライト株式会社 | エポキシ樹脂用硬化促進剤、エポキシ樹脂組成物及び半導体装置 |
| CN103619901B (zh) | 2011-06-24 | 2016-04-06 | 陶氏环球技术有限责任公司 | 热固性组合物和制备纤维增强复合材料的方法 |
| EP2726531B1 (en) | 2011-06-30 | 2015-07-22 | Dow Global Technologies LLC | Curable epoxy resin systems containing mixtures of amine hardeners and an excess of epoxide groups |
| WO2014062407A2 (en) | 2012-10-19 | 2014-04-24 | Dow Global Technologies Llc | Anhydride-cured epoxy resin systems containing divinylarene dioxides |
| BR112015010679A2 (pt) | 2012-11-13 | 2017-07-11 | Dow Global Technologies Llc | sistema de resina epóxi curável, processo para formar um compósito de epóxi reforçado com fibra e compósito reforçado com fibra curada |
| KR102131211B1 (ko) | 2012-11-13 | 2020-07-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 수지 이송 성형 공정을 위한 폴리에틸렌 테트라아민을 함유하는 에폭시 수지 시스템 |
| WO2015119881A1 (en) | 2014-02-07 | 2015-08-13 | Dow Global Technologies Llc | Fast curing high glass transition temperature epoxy resin system |
| EP3218421B1 (en) | 2014-11-11 | 2020-03-11 | Dow Global Technologies LLC | Fast curing high glass transition temperature epoxy resin system |
| EP3313913B1 (en) | 2015-06-25 | 2020-12-30 | Dow Global Technologies LLC | Novel epoxy resin system for making carbon fiber composites |
| US20180179330A1 (en) | 2015-07-07 | 2018-06-28 | Dow Global Technologies, Llc | Stable high glass transition temperature epoxy resin system for making composites |
| US20190194525A1 (en) | 2016-06-21 | 2019-06-27 | Dow Global Technologies Llc | Composition for recovering hydrocarbon fluids from a subterranean reservoir |
| WO2017223490A1 (en) | 2016-06-24 | 2017-12-28 | Dow Global Technologies Llc | Method for reducing the permeability of a subterranean formation to aqueous-based fluids |
| EP3475331A1 (en) | 2016-06-27 | 2019-05-01 | Dow Global Technologies, LLC | Water soluble alpha-glycol sulfonated epoxy resin composition and process for preparing the same |
| WO2018005343A1 (en) | 2016-06-29 | 2018-01-04 | Dow Global Technologies Llc | Method for modifying the permeability to water of a subterranean formation |
| KR102393025B1 (ko) | 2016-08-19 | 2022-05-03 | 다우 글로벌 테크놀로지스 엘엘씨 | 내부 몰드 이형제를 함유하는 에폭시 수지 조성물 |
| EP3592796B1 (en) | 2017-03-09 | 2021-04-21 | Dow Global Technologies LLC | Stable epoxy/internal mold release agent blends for the manufacture of composite articles |
| CN110709444A (zh) | 2017-06-20 | 2020-01-17 | 陶氏环球技术有限责任公司 | 用于制造纤维增强型复合材料的环氧树脂系统 |
| CN108117724A (zh) * | 2017-12-25 | 2018-06-05 | 科化新材料泰州有限公司 | 一种用于半导体封装用的可常温储存型环氧树脂组合物 |
| WO2020005393A1 (en) | 2018-06-26 | 2020-01-02 | Dow Global Technologies Llc | Fibre-reinforced composite and process of making this composite |
| WO2020033037A1 (en) | 2018-08-08 | 2020-02-13 | Dow Global Technologies Llc | Epoxy resin composition |
| WO2020033036A1 (en) | 2018-08-08 | 2020-02-13 | Dow Global Technologies Llc | Epoxy resin composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3477990A (en) * | 1967-12-07 | 1969-11-11 | Shell Oil Co | Process for reacting a phenol with an epoxy compound and resulting products |
| DE2206218A1 (de) | 1972-02-10 | 1973-08-16 | Schering Ag | Verfahren zur herstellung von epoxidharzen |
-
1975
- 1975-05-22 CA CA227,514A patent/CA1041696A/en not_active Expired
- 1975-05-22 CA CA227,512A patent/CA1051031A/en not_active Expired
- 1975-05-22 CA CA227,513A patent/CA1059692A/en not_active Expired
- 1975-05-26 ZA ZA00753392A patent/ZA753392B/xx unknown
- 1975-05-26 ZA ZA00753393A patent/ZA753393B/xx unknown
- 1975-05-26 ZA ZA00753391A patent/ZA753391B/xx unknown
- 1975-06-18 DE DE2559587A patent/DE2559587C3/de not_active Expired
- 1975-06-18 DE DE2559611A patent/DE2559611C3/de not_active Expired
- 1975-06-18 DE DE2527117A patent/DE2527117C3/de not_active Expired
- 1975-06-18 DE DE2527116A patent/DE2527116C3/de not_active Expired
- 1975-06-18 GB GB26032/75A patent/GB1492868A/en not_active Expired
- 1975-06-18 DE DE2527002A patent/DE2527002C2/de not_active Expired
- 1975-06-19 GB GB26193/75A patent/GB1492869A/en not_active Expired
- 1975-06-20 JP JP50074586A patent/JPS5119748A/ja active Pending
- 1975-06-20 BR BR5007/75D patent/BR7503896A/pt unknown
- 1975-06-20 JP JP50074587A patent/JPS5113894A/ja active Pending
- 1975-06-20 CH CH809675A patent/CH618198A5/de not_active IP Right Cessation
- 1975-06-20 CH CH810075A patent/CH618449A5/de not_active IP Right Cessation
- 1975-06-20 BR BR5009/75D patent/BR7503898A/pt unknown
- 1975-06-20 CH CH809575A patent/CH617944A5/de not_active IP Right Cessation
- 1975-06-20 BR BR5008/75D patent/BR7503897A/pt unknown
- 1975-06-20 JP JP50074588A patent/JPS5113895A/ja active Pending
- 1975-06-20 GB GB2634875A patent/GB1464240A/en not_active Expired
- 1975-06-21 ES ES438785A patent/ES438785A1/es not_active Expired
- 1975-06-21 ES ES438786A patent/ES438786A1/es not_active Expired
-
1976
- 1976-04-05 US US05/674,019 patent/US4132706A/en not_active Expired - Lifetime
-
1979
- 1979-11-08 CH CH1002179A patent/CH621564A5/de not_active IP Right Cessation
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| Date | Code | Title | Description |
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| PL | Patent ceased |