CA1215194A - Process for preparing advanced epoxy resins employing tetrahydrocarbyl phosphonium salts as catalysts and advanced epoxy resins prepared by the process - Google Patents
Process for preparing advanced epoxy resins employing tetrahydrocarbyl phosphonium salts as catalysts and advanced epoxy resins prepared by the processInfo
- Publication number
- CA1215194A CA1215194A CA000448454A CA448454A CA1215194A CA 1215194 A CA1215194 A CA 1215194A CA 000448454 A CA000448454 A CA 000448454A CA 448454 A CA448454 A CA 448454A CA 1215194 A CA1215194 A CA 1215194A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- phosphonium
- catalyst
- advanced epoxy
- epoxy 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 83
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 69
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000008569 process Effects 0.000 title claims abstract description 23
- 150000004714 phosphonium salts Chemical class 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 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 title abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 72
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 38
- 239000011347 resin Substances 0.000 claims abstract description 38
- 239000012429 reaction media Substances 0.000 claims abstract description 17
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical group 0.000 claims abstract description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 238000010791 quenching Methods 0.000 claims abstract description 6
- 230000000171 quenching effect Effects 0.000 claims abstract description 6
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000000376 reactant Substances 0.000 claims description 27
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 abstract description 14
- 230000009849 deactivation Effects 0.000 abstract description 9
- 239000000047 product Substances 0.000 description 29
- 150000002118 epoxides Chemical class 0.000 description 20
- -1 qua ternary ammonium halides Chemical class 0.000 description 18
- 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 15
- 150000002989 phenols Chemical class 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229920000180 alkyd Polymers 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229920001567 vinyl ester resin Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000002939 deleterious effect Effects 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 244000236480 Podophyllum peltatum Species 0.000 description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 2
- AKTGKEBIBGSCLD-UHFFFAOYSA-N [ethyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(CC)C1=CC=CC=C1 AKTGKEBIBGSCLD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N alpha-naphthol Natural products C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 125000005497 tetraalkylphosphonium group Chemical group 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
- 230000001052 transient effect Effects 0.000 description 2
- YZLCHCSGEUCERU-UHFFFAOYSA-N (3-ethyloxiran-2-yl)methyl 3-[3-[(3-ethyloxiran-2-yl)methoxy]-3-oxopropyl]sulfanylpropanoate Chemical compound CCC1OC1COC(=O)CCSCCC(=O)OCC1C(CC)O1 YZLCHCSGEUCERU-UHFFFAOYSA-N 0.000 description 1
- PZIYGPCHDBRRRW-UHFFFAOYSA-N (3-methyloxiran-2-yl)methyl 2-(3-methyloxiran-2-yl)acetate Chemical compound CC1OC1COC(=O)CC1C(C)O1 PZIYGPCHDBRRRW-UHFFFAOYSA-N 0.000 description 1
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- DDGXYHGONBCMEX-KTKRTIGZSA-N (Z)-2,3-bis[2-(oxiran-2-yl)ethyl]but-2-enedioic acid Chemical compound C1OC1CC/C(C(O)=O)=C(C(=O)O)\CCC1CO1 DDGXYHGONBCMEX-KTKRTIGZSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-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
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- TXCPKYKDHQFSOC-UHFFFAOYSA-N 2,2-bis[3-(3-tridecyloxiran-2-yl)propyl]propanedioic acid Chemical compound CCCCCCCCCCCCCC1OC1CCCC(C(O)=O)(C(O)=O)CCCC1C(CCCCCCCCCCCCC)O1 TXCPKYKDHQFSOC-UHFFFAOYSA-N 0.000 description 1
- KJMIFCJKRSFFHK-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis[4-(3-nonyloxiran-2-yl)butyl]butanedioic acid Chemical compound CCCCCCCCCC1OC1CCCCC(O)(C(O)=O)C(O)(C(O)=O)CCCCC1C(CCCCCCCCC)O1 KJMIFCJKRSFFHK-UHFFFAOYSA-N 0.000 description 1
- GFDQTSCNSYVIRM-UHFFFAOYSA-N 2-(3-ethyloxiran-2-yl)ethyl 2-(3-methyloxiran-2-yl)acetate Chemical compound CCC1OC1CCOC(=O)CC1C(C)O1 GFDQTSCNSYVIRM-UHFFFAOYSA-N 0.000 description 1
- IMXTVEPTZXBOEA-UHFFFAOYSA-N 2-(3-propyloxiran-2-yl)ethyl 4-[4-oxo-4-[2-(3-propyloxiran-2-yl)ethoxy]butyl]sulfonylbutanoate Chemical compound CCCC1OC1CCOC(=O)CCCS(=O)(=O)CCCC(=O)OCCC1C(CCC)O1 IMXTVEPTZXBOEA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- YTRQUYWMIHVDJI-UHFFFAOYSA-N 2-hydroxy-4-[2-(oxiran-2-yl)ethoxy]-2-[2-[2-(oxiran-2-yl)ethoxy]-2-oxoethyl]-4-oxobutanoic acid Chemical compound C1OC1CCOC(=O)CC(O)(C(=O)O)CC(=O)OCCC1CO1 YTRQUYWMIHVDJI-UHFFFAOYSA-N 0.000 description 1
- ZUYRZVQAOUOSQI-UHFFFAOYSA-N 2-phosphaniumylphenolate Chemical compound OC1=CC=CC=C1P ZUYRZVQAOUOSQI-UHFFFAOYSA-N 0.000 description 1
- PQISOCKFATUOJS-UHFFFAOYSA-N 3-(2-cyclohex-2-en-1-ylpropan-2-yl)cyclohexene Chemical compound C1CCC=CC1C(C)(C)C1CCCC=C1 PQISOCKFATUOJS-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- QWGLNWHWBCINBS-UHFFFAOYSA-N 3-nonylphenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1 QWGLNWHWBCINBS-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical group CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical group CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 241000243251 Hydra Species 0.000 description 1
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- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
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- 241000282320 Panthera leo Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
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- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 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
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- KBWLNCUTNDKMPN-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) hexanedioate Chemical compound C1OC1COC(=O)CCCCC(=O)OCC1CO1 KBWLNCUTNDKMPN-UHFFFAOYSA-N 0.000 description 1
- UTOGBRUNPNKIRC-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] benzene-1,2-dicarboxylate Chemical compound CC1OC1COC(=O)C1=CC=CC=C1C(=O)OCC1C(C)O1 UTOGBRUNPNKIRC-UHFFFAOYSA-N 0.000 description 1
- XEUGWLQVJZLDPM-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] hexanedioate Chemical compound CC1OC1COC(=O)CCCCC(=O)OCC1C(C)O1 XEUGWLQVJZLDPM-UHFFFAOYSA-N 0.000 description 1
- NLGMVWZKXQXENM-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] nonanedioate Chemical compound CC1OC1COC(=O)CCCCCCCC(=O)OCC1C(C)O1 NLGMVWZKXQXENM-UHFFFAOYSA-N 0.000 description 1
- RTTKDGLGHLTZJD-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] oxalate Chemical compound CC1OC1COC(=O)C(=O)OCC1C(C)O1 RTTKDGLGHLTZJD-UHFFFAOYSA-N 0.000 description 1
- IOPXNFITHWTFFE-UHFFFAOYSA-N bis[(3-pentyloxiran-2-yl)methyl] cyclohex-3-ene-1,2-dicarboxylate Chemical compound CCCCCC1OC1COC(=O)C1C(C(=O)OCC2C(O2)CCCCC)C=CCC1 IOPXNFITHWTFFE-UHFFFAOYSA-N 0.000 description 1
- YSJXXOANGNJKMC-UHFFFAOYSA-N bis[(3-pentyloxiran-2-yl)methyl] heptanedioate Chemical compound CCCCCC1OC1COC(=O)CCCCCC(=O)OCC1C(CCCCC)O1 YSJXXOANGNJKMC-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- GELSOTNVVKOYAW-UHFFFAOYSA-N ethyl(triphenyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 GELSOTNVVKOYAW-UHFFFAOYSA-N 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000010460 hemp oil Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical group CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 210000003689 pubic bone Anatomy 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical class [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—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 curing agents used
- C08G59/62—Alcohols or phenols
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/470,107 US4438254A (en) | 1983-02-28 | 1983-02-28 | Process for producing epoxy resins |
| US470,107 | 1983-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1215194A true CA1215194A (en) | 1986-12-09 |
Family
ID=23866303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000448454A Expired CA1215194A (en) | 1983-02-28 | 1984-02-28 | Process for preparing advanced epoxy resins employing tetrahydrocarbyl phosphonium salts as catalysts and advanced epoxy resins prepared by the process |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4438254A (enExample) |
| EP (1) | EP0117562B1 (enExample) |
| JP (1) | JPS60500626A (enExample) |
| KR (1) | KR860000809B1 (enExample) |
| AU (1) | AU562868B2 (enExample) |
| BR (1) | BR8406168A (enExample) |
| CA (1) | CA1215194A (enExample) |
| DE (1) | DE3475717D1 (enExample) |
| ES (1) | ES8600339A1 (enExample) |
| GB (1) | GB2135674B (enExample) |
| MY (1) | MY8800004A (enExample) |
| NO (1) | NO161070C (enExample) |
| NZ (1) | NZ207301A (enExample) |
| WO (1) | WO1984003289A1 (enExample) |
| ZA (1) | ZA841476B (enExample) |
Families Citing this family (90)
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|---|---|---|---|---|
| US4594291A (en) * | 1984-07-17 | 1986-06-10 | The Dow Chemical Company | Curable, partially advanced epoxy resins |
| US5503937A (en) * | 1984-07-17 | 1996-04-02 | The Dow Chemical Company | Curable composition which comprises adducts of heterocyclic compounds |
| NZ212747A (en) * | 1984-07-17 | 1989-01-27 | Dow Chemical Co | Partially advanced epoxy resin compositions |
| US4946817A (en) * | 1984-07-17 | 1990-08-07 | The Dow Chemical Company | Latent catalysts for epoxy-containing compounds |
| GB8420816D0 (en) * | 1984-08-16 | 1984-09-19 | Dow Chemical Rheinwerk Gmbh | Epoxy resins |
| US4604317A (en) * | 1984-10-05 | 1986-08-05 | The Dow Chemical Company | Curable compositions containing a polyepoxide and a halogenated bisphenol |
| US4568735A (en) * | 1984-11-05 | 1986-02-04 | Shell Oil Company | Process for preparing polyepoxides (II) |
| DE3583395D1 (en) * | 1984-12-04 | 1991-08-08 | Dow Chemical Co | Hitzestabiles thermoplastisches harz. |
| US4612156A (en) * | 1985-02-26 | 1986-09-16 | The Dow Chemical Company | Solventless process for producing resinous materials |
| US4721743A (en) * | 1985-03-25 | 1988-01-26 | The Dow Chemical Company | Non-thermoset thermally stable capped epoxy resin compositions |
| US4783509A (en) * | 1985-03-25 | 1988-11-08 | The Dow Chemical Company | Non-thermoset thermally stable capped epoxy resin compositions |
| US4596861A (en) * | 1985-05-22 | 1986-06-24 | The Dow Chemical Company | Advanced epoxy resin for can coating applications |
| US4634757A (en) * | 1985-07-15 | 1987-01-06 | Shell Oil Company | Fusion product |
| GB8519290D0 (en) * | 1985-07-31 | 1985-09-04 | Dow Chemical Rheinwerk Gmbh | Resin composition |
| US4647648A (en) * | 1985-08-26 | 1987-03-03 | The Dow Chemical Company | Polyhydroxyethers from hydroxybiphenyls |
| US4684700A (en) * | 1986-02-14 | 1987-08-04 | The Dow Chemical Company | Advanced epoxy resins prepared from triglycidyl ethers and dihydri phenols |
| US4692504A (en) * | 1986-04-30 | 1987-09-08 | Shell Oil Company | Deactivation of phosphonium salt catalyst |
| US4732958A (en) * | 1986-12-30 | 1988-03-22 | Shell Oil Company | Epoxy fusion process |
| US4829141A (en) * | 1987-07-31 | 1989-05-09 | Shell Oil Company | Epoxy fusion catalyst and process |
| US4880892A (en) * | 1987-08-31 | 1989-11-14 | Ciba-Geigy Corporation | Composition comprising an epoxy resin, a phenol and an advancement catalyst |
| JPH0219171U (enExample) * | 1988-07-22 | 1990-02-08 | ||
| US4933420A (en) * | 1988-09-23 | 1990-06-12 | The Dow Chemical Company | Epoxy resins containing phosphonium catalysts |
| US5105006A (en) * | 1989-05-25 | 1992-04-14 | The Dow Chemical Company | Phosphonium salts |
| US5045632A (en) * | 1989-05-25 | 1991-09-03 | The Dow Chemical Company | Novel bis(phosphoranylidene) ammonium salts |
| US5310854A (en) * | 1989-08-23 | 1994-05-10 | The Dow Chemical Company | Epoxy resin composition and process therefor |
| US4981926A (en) * | 1990-02-06 | 1991-01-01 | The Dow Chemical Company | Composition of epoxy resin, amino group-containing phosphonium catalyst and curing agent |
| BR9100475A (pt) * | 1990-02-06 | 1991-10-29 | Dow Chemical Co | Aduto,complexo ou composto,composicao,processo para a preparacao de um aduto,complexo ou composto e processo para a preparacao de uma composicao |
| US5208317A (en) * | 1990-02-06 | 1993-05-04 | The Dow Chemical Company | Composition comprising epoxy resin and cationic amine phosphonium catalyst |
| US5169473A (en) * | 1990-05-21 | 1992-12-08 | The Dow Chemical Company | Latent catalysts, epoxy compositions incorporating same, and coating, impregnating and bonding methods employing the compositions |
| ZA913801B (en) * | 1990-05-21 | 1993-01-27 | Dow Chemical Co | Latent catalysts,cure-inhibited epoxy resin compositions and laminates prepared therefrom |
| US5721323A (en) * | 1990-05-21 | 1998-02-24 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| 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 |
| US6011111A (en) * | 1993-10-18 | 2000-01-04 | The Dow Chemical Company | Hydroxy-phenoxyether polymer thermoplastic composites |
| AR006683A1 (es) * | 1996-04-19 | 1999-09-08 | Shell Int Research | Un procedimiento para la preparacion de una resina avanzada, y una composicion curada obtenida mediante el uso de dicha resina |
| US6613839B1 (en) * | 1997-01-21 | 2003-09-02 | The Dow Chemical Company | Polyepoxide, catalyst/cure inhibitor complex and anhydride |
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| US5962621A (en) * | 1998-04-28 | 1999-10-05 | The Dow Chemical Company | Process for preparing hydroxy-functionalized polyesters |
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| US20220002564A1 (en) | 2018-10-17 | 2022-01-06 | Dow Global Technologies Llc | A coating composition, a coated fabric, a method of making a coated fabric, and an article made from the coated fabric |
| CA3117663C (en) | 2018-11-15 | 2024-06-11 | Zephyros, Inc. | Two-component phosphate ester cavity filling semi rigid foam |
| JP7273978B2 (ja) | 2019-04-03 | 2023-05-15 | ゼフィロス インコーポレイテッド | 二部リン酸エステルエポキシ組成物 |
| US11673995B2 (en) * | 2019-08-08 | 2023-06-13 | Ppg Industries Ohio, Inc. | Polyol polymers, methods of preparing such polymers, and coating compositions containing the same |
| US20230101875A1 (en) | 2020-02-24 | 2023-03-30 | Zephyros, Inc. | Ballistic composition, ballistic assembly, and method therefor |
| US12391792B2 (en) | 2020-08-05 | 2025-08-19 | Blue Cube Ip Llc | Hardener formulation for cold curing epoxy systems |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1101739A (en) * | 1964-06-08 | 1968-01-31 | Celanese Coatings Co | High molecular weight thermoplastic polyhydroxypolyethers |
| NL137295C (enExample) | 1965-11-03 | |||
| US3477990A (en) | 1967-12-07 | 1969-11-11 | Shell Oil Co | Process for reacting a phenol with an epoxy compound and resulting products |
| US3547885A (en) | 1968-03-08 | 1970-12-15 | Sun Oil Co | Process for curing polyepoxides with anhydrides and phosphonium halide catalysts therefor |
| NL6915348A (enExample) * | 1968-10-25 | 1970-04-28 | ||
| FR2086192B1 (enExample) * | 1970-04-20 | 1974-02-15 | Shell Int Research | |
| US3694407A (en) | 1970-08-11 | 1972-09-26 | Shell Oil Co | Epoxy-containing condensates,their preparation and use |
| US3948855A (en) | 1971-09-16 | 1976-04-06 | The Dow Chemical Company | Process for reacting a phenol with a vicinal epoxy compound in the presence of phosphorus or carbon containing acid, ester or acid ester |
| US3738862A (en) | 1971-11-08 | 1973-06-12 | Shell Oil Co | Process for preparing reinforced laminates in situ with epoxy-polyhydric phenol condensates |
| US4171420A (en) | 1974-06-21 | 1979-10-16 | The Dow Chemical Company | Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids |
| CA1041696A (en) * | 1974-06-21 | 1978-10-31 | George A. Doorakian | Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids |
| GB1494972A (en) * | 1976-01-19 | 1977-12-14 | Dow Chemical Co | Process of reacting epoxides with phenols carboxylic acids or carboxylic acid anhydrides |
| US4048141A (en) | 1975-11-06 | 1977-09-13 | The Dow Chemical Company | Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids |
| US4104257A (en) * | 1977-07-27 | 1978-08-01 | The Dow Chemical Company | Process for preparing high molecular weight polyether resins from bisphenols and epoxy resins |
| US4122067A (en) * | 1977-10-07 | 1978-10-24 | Celanese Polymer Specialties Company | Process of reacting a polyepoxide compound with a phenol in aqueous medium |
| GB1580603A (en) * | 1978-05-18 | 1980-12-03 | Dow Chemical Co | Process for preparing triorgano-(2,5-dihydroxyphenyl) phosphonium salts |
| US4370465A (en) * | 1980-12-04 | 1983-01-25 | The Dow Chemical Co. | 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 |
| US4389520A (en) | 1982-04-05 | 1983-06-21 | Ciba-Geigy Corporation | Advancement catalysts for epoxy resins |
| WO1983004414A1 (en) * | 1982-06-10 | 1983-12-22 | The Dow Chemical Company | Advanced epoxy resins and coating compositions containing the advanced epoxy resins |
-
1983
- 1983-02-28 US US06/470,107 patent/US4438254A/en not_active Expired - Fee Related
-
1984
- 1984-02-21 AU AU26942/84A patent/AU562868B2/en not_active Ceased
- 1984-02-21 JP JP59501231A patent/JPS60500626A/ja active Granted
- 1984-02-21 WO PCT/US1984/000239 patent/WO1984003289A1/en not_active Ceased
- 1984-02-21 BR BR8406168A patent/BR8406168A/pt not_active IP Right Cessation
- 1984-02-28 EP EP84102067A patent/EP0117562B1/en not_active Expired
- 1984-02-28 NZ NZ207301A patent/NZ207301A/en unknown
- 1984-02-28 NO NO840748A patent/NO161070C/no unknown
- 1984-02-28 GB GB08405154A patent/GB2135674B/en not_active Expired
- 1984-02-28 ZA ZA841476A patent/ZA841476B/xx unknown
- 1984-02-28 KR KR1019840000988A patent/KR860000809B1/ko not_active Expired
- 1984-02-28 DE DE8484102067T patent/DE3475717D1/de not_active Expired
- 1984-02-28 ES ES530107A patent/ES8600339A1/es not_active Expired
- 1984-02-28 CA CA000448454A patent/CA1215194A/en not_active Expired
-
1988
- 1988-12-30 MY MY4/88A patent/MY8800004A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU562868B2 (en) | 1987-06-18 |
| JPS632971B2 (enExample) | 1988-01-21 |
| US4438254A (en) | 1984-03-20 |
| KR860000809B1 (ko) | 1986-06-28 |
| GB2135674B (en) | 1986-08-28 |
| NO161070C (no) | 1989-06-28 |
| WO1984003289A1 (en) | 1984-08-30 |
| NO840748L (no) | 1984-08-29 |
| ES530107A0 (es) | 1985-05-01 |
| BR8406168A (pt) | 1985-03-12 |
| KR840007736A (ko) | 1984-12-10 |
| JPS60500626A (ja) | 1985-05-02 |
| AU2694284A (en) | 1984-09-10 |
| EP0117562B1 (en) | 1988-12-21 |
| NZ207301A (en) | 1987-10-30 |
| ES8600339A1 (es) | 1985-05-01 |
| NO161070B (no) | 1989-03-20 |
| MY8800004A (en) | 1988-12-31 |
| EP0117562A2 (en) | 1984-09-05 |
| DE3475717D1 (en) | 1989-01-26 |
| GB8405154D0 (en) | 1984-04-04 |
| EP0117562A3 (en) | 1985-09-04 |
| GB2135674A (en) | 1984-09-05 |
| ZA841476B (en) | 1985-10-30 |
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