CS236685B2 - Preparation method of thermoset substance containing oxazoline and urethane bonds - Google Patents
Preparation method of thermoset substance containing oxazoline and urethane bonds Download PDFInfo
- Publication number
- CS236685B2 CS236685B2 CS827210A CS721082A CS236685B2 CS 236685 B2 CS236685 B2 CS 236685B2 CS 827210 A CS827210 A CS 827210A CS 721082 A CS721082 A CS 721082A CS 236685 B2 CS236685 B2 CS 236685B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- prepolymer
- equivalent weight
- mixture
- oxazolidone
- groups
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 title abstract description 17
- 239000000126 substance Substances 0.000 title description 12
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 17
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 15
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 12
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 10
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 10
- 239000002202 Polyethylene glycol Substances 0.000 claims description 24
- 229920001223 polyethylene glycol Polymers 0.000 claims description 24
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 21
- 239000012948 isocyanate Substances 0.000 claims description 20
- 150000002513 isocyanates Chemical class 0.000 claims description 19
- -1 aromatic anhydride Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000005580 one pot reaction Methods 0.000 claims description 4
- 229920003986 novolac Polymers 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012744 reinforcing agent Substances 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 68
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 15
- 150000002148 esters Chemical class 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 description 47
- 239000000047 product Substances 0.000 description 40
- 239000003054 catalyst Substances 0.000 description 34
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 27
- 125000005442 diisocyanate group Chemical group 0.000 description 21
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 18
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 13
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 12
- 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 12
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 12
- 239000012975 dibutyltin dilaurate Substances 0.000 description 11
- 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 10
- 150000008064 anhydrides Chemical class 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003365 glass fiber Substances 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 4
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- 239000004970 Chain extender Substances 0.000 description 3
- XPPWXDNYGJIOPW-UHFFFAOYSA-N O1[C-]=NC(C1)=O.NC(=O)OCC Chemical compound O1[C-]=NC(C1)=O.NC(=O)OCC XPPWXDNYGJIOPW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000005275 alkylenearyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 239000005337 ground glass Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- BBXFVDGUPMYLQO-UHFFFAOYSA-N 2H-pyrrol-2-id-3-one Chemical compound N1=[C-]C(C=C1)=O BBXFVDGUPMYLQO-UHFFFAOYSA-N 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 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
- 239000004604 Blowing Agent Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 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
- 230000000996 additive effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 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 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- PGCIRCHPCBYSEC-UHFFFAOYSA-M lithium;n-[bis(dimethylamino)phosphoryl]-n-methylmethanamine;chloride Chemical compound [Li+].[Cl-].CN(C)P(=O)(N(C)C)N(C)C PGCIRCHPCBYSEC-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
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
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
- C08G18/581—Reaction products of epoxy resins with less than equivalent amounts of compounds containing active hydrogen added before or during the reaction with the isocyanate component
-
- 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
- C08G2120/00—Compositions for reaction injection moulding processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/309,737 US4386191A (en) | 1981-10-08 | 1981-10-08 | Compositions for forming poly(oxazolidone/urethane) thermosets and products therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236685B2 true CS236685B2 (en) | 1985-05-15 |
Family
ID=23199462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS827210A CS236685B2 (en) | 1981-10-08 | 1982-10-08 | Preparation method of thermoset substance containing oxazoline and urethane bonds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4386191A (fr) |
| EP (1) | EP0077174B1 (fr) |
| JP (1) | JPS5871916A (fr) |
| KR (1) | KR890003128B1 (fr) |
| CA (1) | CA1204548A (fr) |
| CS (1) | CS236685B2 (fr) |
| DD (1) | DD208625A5 (fr) |
| DE (1) | DE3279920D1 (fr) |
| ES (1) | ES516313A0 (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504633A (en) * | 1983-06-01 | 1985-03-12 | Stauffer Chemical Company | Modified poly(oxazolidone/urethane) compositions |
| US4605711A (en) * | 1983-06-01 | 1986-08-12 | Stauffer Chemical Company | Modified poly(oxazolidone/urethane) compositions |
| CA1250987A (fr) * | 1983-10-17 | 1989-03-07 | Gerald Fesman | Melange d'ignifugation pour materiaux a base de polyurethane |
| US4613660A (en) * | 1985-02-19 | 1986-09-23 | Ashland Oil, Inc. | Polyol/polyepoxide/polyurethane adhesive |
| US4726868A (en) * | 1985-02-19 | 1988-02-23 | Ashland Oil, Inc. | Polyol/polyepoxide/polyurethane adhesive |
| US4612156A (en) * | 1985-02-26 | 1986-09-16 | The Dow Chemical Company | Solventless process for producing resinous materials |
| US4614786A (en) * | 1985-08-12 | 1986-09-30 | Ashland Oil Inc. | Stable isocyanate/epoxide prepolymers and thermoset polyurethanes produced therefrom |
| JPS6259670A (ja) * | 1985-09-09 | 1987-03-16 | Kansai Paint Co Ltd | 樹脂被覆用組成物 |
| EP0305331A3 (fr) * | 1987-08-25 | 1991-05-08 | Ciba-Geigy Ag | Flexibilisateurs pour résines époxydes |
| JPH0436307A (ja) * | 1990-06-01 | 1992-02-06 | Yuka Shell Epoxy Kk | 変性エポキシ樹脂及びエポキシ樹脂塗料 |
| US5049281A (en) * | 1990-12-06 | 1991-09-17 | Exxon Research And Engineering Company | Multi-block polymer comprising a first prepolymer, made by combining epoxy with diamine, chain extended with a compatible second prepolymer, the membrane made therefrom and its use in separations |
| US5039422A (en) * | 1990-12-06 | 1991-08-13 | Exxon Research And Engineering Company | Multi-block polymer comprising a urea prepolymer chain extended with a compatible second prepolymer, the membrane made therefrom and its use in separations |
| US5221481A (en) * | 1990-12-06 | 1993-06-22 | Exxon Research And Engineering Company | Multi-block polymer comprising an ester prepolymer, made by combining epoxy with polyester, chain extended with a compatible second prepolymer, the membrane made therefrom and its use for separations |
| US5130017A (en) * | 1990-12-06 | 1992-07-14 | Exxon Research And Engineering Company | Multi-block polymer comprising a first amide acid prepolymer, chain extended with a compatible second prepolymer, the membrane made therefrom and its use in separations |
| US5039418A (en) * | 1990-12-06 | 1991-08-13 | Exxon Research And Engineering Company | Membrane made from a multi-block polymer comprising an oxazolidone prepolymer chain extended with a compatible second prepolymer and its use in separations |
| US5039417A (en) * | 1990-12-06 | 1991-08-13 | Exxon Research And Engineering Company | Membrane made from a multi-block polymer comprising an imide or amide-acid prepolymer chain extended with a compatible second prepolymer and its use in separations |
| US5237076A (en) * | 1992-08-28 | 1993-08-17 | The Aerospace Corporation | Preparation of liquid crystalline di(alkoxyglycidyl) compounds, and their use in curable epoxide mixtures |
| EP2072556A1 (fr) * | 2007-12-17 | 2009-06-24 | Sika Technology AG | Procédé de fabrication de polymères hydroxyfonctionnels, produits de polyaddition à terminaison de groupes isocyanates ainsi obtenus et leur utilisation |
| US9637586B2 (en) * | 2015-02-12 | 2017-05-02 | Uop Llc | High temperature resistant epoxy resins for producing hollow fiber membrane modules for high temperature gas separation applications |
| CN110144035A (zh) * | 2019-05-24 | 2019-08-20 | 桂林电子科技大学 | 一种聚乙二醇接枝环氧树脂复合材料及其制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142657A (en) * | 1949-08-12 | 1964-07-28 | Ciba Ltd | Elastic reaction product of a polyepoxide, a glycol, and an acid anhydride |
| US2891034A (en) * | 1949-08-12 | 1959-06-16 | Ciba Ltd | Composition comprising a reaction product of a polyester and a polyepoxide and process for preparation |
| CH410430A (de) * | 1955-12-19 | 1966-10-31 | Minnesota Mining & Mfg | Verfahren zur Herstellung gehärter Harze und Anwendung desselben |
| US2947717A (en) * | 1956-06-11 | 1960-08-02 | Devoe & Raynolds Co Inc | Epoxide resin compositions |
| BE563324A (fr) * | 1956-12-20 | |||
| US3299008A (en) * | 1958-12-23 | 1967-01-17 | Shell Oil Co | Process for preparing flexible resinified products from polyepoxides and resulting products |
| US3294865A (en) * | 1965-12-13 | 1966-12-27 | Celanese Coatings Company Inc | Curing of epoxy resins with polycarboxylates, polyhydric phenols or polyhydric alcohols and, as an accelerator, an alkali metal salt |
| US3507820A (en) * | 1966-10-13 | 1970-04-21 | Dainippon Ink & Chemicals | Process for preparing a polyester compound from epoxy resin material obtained from 2-methylepichlorohydrin |
| CH487962A (de) * | 1968-02-19 | 1970-03-31 | Ciba Geigy | In kristalline Kunststoffprodukte umwandelbare Formmassen auf Basis von Diepoxiden und Polyester-dicarbonsäuren |
| US3576903A (en) * | 1968-04-29 | 1971-04-27 | Minnesota Mining & Mfg | Epoxy-terminated adducts of carboxy terminated polyesters and polyepoxides |
| JPS4940863B1 (fr) * | 1970-01-22 | 1974-11-06 | ||
| US3687897A (en) * | 1970-06-22 | 1972-08-29 | Dow Chemical Co | Preparation of oxazolidinones by reacting an isocyanate, or isothiocyanate with an epoxide in the presence of a phosphonium halide acid, ester, or acid ester of the element c |
| JPS5133905B2 (fr) * | 1972-04-14 | 1976-09-22 |
-
1981
- 1981-10-08 US US06/309,737 patent/US4386191A/en not_active Expired - Fee Related
-
1982
- 1982-10-06 EP EP82305312A patent/EP0077174B1/fr not_active Expired
- 1982-10-06 DE DE8282305312T patent/DE3279920D1/de not_active Expired
- 1982-10-06 DD DD82243837A patent/DD208625A5/de unknown
- 1982-10-07 KR KR8204517A patent/KR890003128B1/ko not_active Expired
- 1982-10-07 CA CA000413021A patent/CA1204548A/fr not_active Expired
- 1982-10-07 ES ES516313A patent/ES516313A0/es active Granted
- 1982-10-08 JP JP57176467A patent/JPS5871916A/ja active Pending
- 1982-10-08 CS CS827210A patent/CS236685B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD208625A5 (de) | 1984-04-04 |
| EP0077174A3 (en) | 1983-08-24 |
| ES8403955A1 (es) | 1984-04-01 |
| JPS5871916A (ja) | 1983-04-28 |
| EP0077174A2 (fr) | 1983-04-20 |
| ES516313A0 (es) | 1984-04-01 |
| KR890003128B1 (ko) | 1989-08-23 |
| EP0077174B1 (fr) | 1989-09-06 |
| CA1204548A (fr) | 1986-05-13 |
| KR840002011A (ko) | 1984-06-11 |
| DE3279920D1 (en) | 1989-10-12 |
| US4386191A (en) | 1983-05-31 |
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