CS236490B2 - Method of thermosetting mass preparation containing oxazolidon and urethan linkages - Google Patents

Method of thermosetting mass preparation containing oxazolidon and urethan linkages Download PDF

Info

Publication number: CS236490B2
Authority: CS; Czechoslovakia
Prior art keywords: prepolymer; reaction; oxazolidone; diglycidyl ether; mixture
Prior art date: 1981-10-08

Application number

CS827209A

Other languages

Czech (cs)

English (en)

Inventor

Salvo Anthony L Di

Yu Arturjun Shen

Original Assignee

Stauffer Chemical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-10-08

Filing date

1982-10-08

Publication date

1985-05-15

1982-10-08 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1985-05-15 Publication of CS236490B2 publication Critical patent/CS236490B2/cs

Links

JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims abstract description 16
229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 12
WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical compound O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 4
229920000642 polymer Polymers 0.000 claims abstract description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
125000003700 epoxy group Chemical group 0.000 claims abstract description 14
238000004519 manufacturing process Methods 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 39
239000003054 catalyst Substances 0.000 claims description 32
230000015572 biosynthetic process Effects 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 17
239000004593 Epoxy Substances 0.000 claims description 15
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 14
239000011541 reaction mixture Substances 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
150000004703 alkoxides Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
229910001507 metal halide Inorganic materials 0.000 claims description 2
150000005309 metal halides Chemical class 0.000 claims description 2
229920000768 polyamine Polymers 0.000 claims description 2
150000001991 dicarboxylic acids Chemical class 0.000 claims 2
150000004985 diamines Chemical class 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
150000002763 monocarboxylic acids Chemical class 0.000 claims 1
229920003986 novolac Polymers 0.000 claims 1
150000002902 organometallic compounds Chemical class 0.000 claims 1
150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
229920005989 resin Polymers 0.000 claims 1
239000011347 resin Substances 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 57
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 abstract description 31
229920001228 polyisocyanate Polymers 0.000 abstract description 9
239000005056 polyisocyanate Substances 0.000 abstract description 9
150000002148 esters Chemical class 0.000 abstract description 6
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract description 3
229920005862 polyol Polymers 0.000 description 19
150000003077 polyols Chemical class 0.000 description 18
125000005442 diisocyanate group Chemical group 0.000 description 13
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 13
239000011521 glass Substances 0.000 description 12
239000000243 solution Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
239000000376 reactant Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
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 8
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
239000012975 dibutyltin dilaurate Substances 0.000 description 6
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
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 5
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
-1 welt Substances 0.000 description 5
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 4
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 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000000178 monomer Substances 0.000 description 4
229920000098 polyolefin Polymers 0.000 description 4
239000004814 polyurethane Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 3
239000001361 adipic acid Substances 0.000 description 3
235000011037 adipic acid Nutrition 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
150000002118 epoxides Chemical group 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
239000007787 solid Substances 0.000 description 3
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
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 2
239000000654 additive Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004429 atom 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
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000005266 casting Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229940049964 oleate Drugs 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
OWMNWOXJAXJCJI-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxymethyl)oxirane;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1OC1COCC1CO1 OWMNWOXJAXJCJI-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
241001239379 Calophysus macropterus Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
238000007872 degassing Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
125000001142 dicarboxylic acid group Chemical group 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
206010013023 diphtheria Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
POMZBEGASDKMRR-UHFFFAOYSA-M lithium;cyanate Chemical compound [Li+].[O-]C#N POMZBEGASDKMRR-UHFFFAOYSA-M 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
BTAUEIDLAAYHSL-UHFFFAOYSA-M lithium;octanoate Chemical compound [Li+].CCCCCCCC([O-])=O BTAUEIDLAAYHSL-UHFFFAOYSA-M 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical group [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
UHEOCPAMGZSLMB-UHFFFAOYSA-N phenol A acid Natural products CC(O)C(C)C1=CC(O)=C(C(O)=O)C(O)=C1C UHEOCPAMGZSLMB-UHFFFAOYSA-N 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000007039 two-step reaction Methods 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
- 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4284—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with other curing 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
- 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
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors 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
- C08G59/14—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
- C08G2120/00—Compositions for reaction injection moulding processes

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Emergency Medicine (AREA)
General Chemical & Material Sciences (AREA)
Polyurethanes Or Polyureas (AREA)

CS827209A 1981-10-08 1982-10-08 Method of thermosetting mass preparation containing oxazolidon and urethan linkages CS236490B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/309,732 US4424316A (en)	1981-10-08	1981-10-08	Compositions for forming poly(oxazolidone/urethane) thermosets and products therefrom

Publications (1)

Publication Number	Publication Date
CS236490B2 true CS236490B2 (en)	1985-05-15

Family

ID=23199436

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS827209A CS236490B2 (en)	1981-10-08	1982-10-08	Method of thermosetting mass preparation containing oxazolidon and urethan linkages

Country Status (10)

Country	Link
US (1)	US4424316A (ko)
EP (1)	EP0077175B1 (ko)
JP (1)	JPS5871914A (ko)
KR (1)	KR890003002B1 (ko)
BR (1)	BR8205890A (ko)
CA (1)	CA1210889A (ko)
CS (1)	CS236490B2 (ko)
DD (1)	DD203055A5 (ko)
DE (1)	DE3275298D1 (ko)
ES (1)	ES8403954A1 (ko)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
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US4504633A (en) *	1983-06-01	1985-03-12	Stauffer Chemical Company	Modified poly(oxazolidone/urethane) compositions
FR2549277B1 (fr) *	1983-07-13	1985-10-25	Alsthom Atlantique	Procede d'isolation par impregnation d'un bobinage electrique, et vernis sans solvant stabilise utilisable dans ce procede
CA1340052C (en) *	1988-03-31	1998-09-22	Narasimhan Raghupathi	Chemically treated glass fibers for reinforcing thermosetting polymer matrices
EP0342064B1 (en) *	1988-05-13	1995-02-15	Nippon Paint Co., Ltd.	A thermosetting resinous composition and preparation of heat resisting coating and molded product using said composition
US4981754A (en) *	1988-06-20	1991-01-01	Owens-Corning Fiberglas Corporation	Glass fibers having a size composition containing the reaction product of an acid and/or alcohol with the terminal epoxy groups of a diglycidyl ether of a bisphenol
JPH03255122A (ja) *	1990-03-02	1991-11-14	Nippon Paint Co Ltd	熱硬化性樹脂組成物ならびに熱硬化樹脂成形物
US5138016A (en) *	1990-12-18	1992-08-11	H. B. Fuller Company	Isocyanurate-free oxazolidone compound made from epoxy and a hindered isocyanate compound and a novel catalyst for their production
US5304612A (en) *	1990-12-25	1994-04-19	Teijin Limited	Plural liquid pack type heat curable polyisocyanate-glycidyl acrylate compound resinous composition and process for producing shaped resin article therefrom
US5480958A (en) *	1994-09-21	1996-01-02	Air Products And Chemicals, Inc.	Polyepoxide resins incorporating epoxy terminated urethanes as tougheners
DE19654149A1 (de) *	1996-12-23	1998-06-25	Basf Ag	Oxazolidon- und Urethangruppen enthaltende, unter Druck stehende isocyanatterminierte Prepolymere für Einkomponenten-Schäume
US7267288B2 (en) *	2001-03-22	2007-09-11	Nevada Supply Corporation	Polyurethane in intimate contact with fibrous material
US7599861B2 (en)	2006-03-02	2009-10-06	Convergys Customer Management Group, Inc.	System and method for closed loop decisionmaking in an automated care system
US8379830B1 (en)	2006-05-22	2013-02-19	Convergys Customer Management Delaware Llc	System and method for automated customer service with contingent live interaction
US7809663B1 (en)	2006-05-22	2010-10-05	Convergys Cmg Utah, Inc.	System and method for supporting the utilization of machine language

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US2830038A (en)	1957-05-07	1958-04-08	Du Pont	Poly (polyalkylene ether urethane) polymers containing terminal epoxide groups
US3242108A (en)	1961-04-04	1966-03-22	Union Carbide Corp	Compositions for producing polyurethane resins and resinous foams and products prepared therefrom
NL280840A (ko)	1961-07-12
US3313747A (en)	1964-10-29	1967-04-11	Baker Chem Co J T	Polymers prepared from isocyanateoxazolidinones
US3373221A (en)	1964-11-04	1968-03-12	Shell Oil Co	Reaction products of unsaturated esters of polyepoxides and unsaturated carboxylic acids, and polyisocyanates
US3445436A (en)	1966-06-14	1969-05-20	Tremco Mfg Co	Polyurethane polyepoxides
US3761452A (en)	1968-02-16	1973-09-25	Du Pont	Epoxy polyurethane prepolymer compositions which are self curing uponapplication of heat
US3484413A (en)	1968-04-29	1969-12-16	Mobay Chemical Corp	Polyurethanes prepared from the cyclization product of a polyglycidyl carbamate
US3639655A (en)	1969-03-21	1972-02-01	Phillips Petroleum Co	Preparation of hydroxy-substituted polyesters
JPS4940863B1 (ko)	1970-01-22	1974-11-06
DE2247696A1 (de)	1972-09-28	1974-05-02	Synthopol Chemie Dr Koch	Verfahren zur herstellung von waermehaertbaren ueberzuegen
US3781235A (en)	1972-10-31	1973-12-25	Gen Electric	Method for making rigid foam and compositions using such method
US4070416A (en)	1972-11-29	1978-01-24	Hitachi, Ltd.	Novel thermosetting resin and a process for producing same
JPS5727894B2 (ko) *	1974-10-11	1982-06-14
FR2291996A1 (fr) *	1974-11-20	1976-06-18	Rhone Poulenc Ind	Polymeres nouveaux prepares a partir de polyisocyanates et de polyepoxydes
DE2557408C2 (de)	1975-12-19	1983-08-25	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung eines in organischen Lösungsmitteln löslichen, vernetzbaren Acryloyl- und/oder Methacryloylgruppen und Carboxylgruppen enthaltenden Urethanharzes und seine Verwendung
US4066628A (en)	1976-08-02	1978-01-03	Mitsubishi Chemical Industries Ltd.	Oxazolidone catalyst
US4143009A (en)	1977-03-02	1979-03-06	Frank Dewey	Polyurethane-epoxy casting resin
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US4239857A (en)	1978-06-29	1980-12-16	Union Carbide Corporation	Process for producing solid or microcellular polyurethane elastomers having improved green strength

1981
- 1981-10-08 US US06/309,732 patent/US4424316A/en not_active Expired - Fee Related
1982
- 1982-10-06 EP EP82305313A patent/EP0077175B1/en not_active Expired
- 1982-10-06 DD DD82243838A patent/DD203055A5/de unknown
- 1982-10-06 DE DE8282305313T patent/DE3275298D1/de not_active Expired
- 1982-10-07 ES ES516312A patent/ES8403954A1/es not_active Expired
- 1982-10-07 BR BR8205890A patent/BR8205890A/pt unknown
- 1982-10-07 KR KR8204516A patent/KR890003002B1/ko active
- 1982-10-07 CA CA000413010A patent/CA1210889A/en not_active Expired
- 1982-10-08 JP JP57176466A patent/JPS5871914A/ja active Pending
- 1982-10-08 CS CS827209A patent/CS236490B2/cs unknown

Also Published As

Publication number	Publication date
EP0077175A3 (en)	1983-08-24
US4424316A (en)	1984-01-03
BR8205890A (pt)	1983-09-06
KR840002010A (ko)	1984-06-11
KR890003002B1 (ko)	1989-08-18
DD203055A5 (de)	1983-10-12
DE3275298D1 (en)	1987-03-05
CA1210889A (en)	1986-09-02
ES516312A0 (es)	1984-04-01
JPS5871914A (ja)	1983-04-28
EP0077175A2 (en)	1983-04-20
ES8403954A1 (es)	1984-04-01
EP0077175B1 (en)	1987-01-28

Publication	Publication Date	Title
CA1328946C (en)	1994-04-26	Two stage process for the production of molded articles
CS236490B2 (en)	1985-05-15	Method of thermosetting mass preparation containing oxazolidon and urethan linkages
JP2559094B2 (ja)	1996-11-27	成形品の製造方法
KR100423468B1 (ko)	2004-06-30	지방족폴리이소시아네이트및폴리에스테르에테르폴리올로부터제조된폴리우레탄엘라스토머
CA1270847A (en)	1990-06-26	Thermoset molding compositions
JP5728383B2 (ja)	2015-06-03	イソシアネート系強靱化剤を含んでなるベンゾオキサジン系組成物
US3912566A (en)	1975-10-14	Method for bonding surfaces together using a mixture of an epoxide resin, a poly(aminoamide) and blocked isocyanate prepolymer
CN1294604A (zh)	2001-05-09	非弹性体聚氨酯组合物
EP0077174B1 (en)	1989-09-06	Compositions for forming poly(oxazolidone/urethane)thermosets
JPS61218617A (ja)	1986-09-29	ポリオキシペルフルオロアルキレンのブロツクを含むフツ化ポリウレタン及びその製造方法
EP0169066B1 (en)	1989-02-22	Fast curing expoxy resin compositions
US4632970A (en)	1986-12-30	Epoxy resin composition
JPH05140253A (ja)	1993-06-08	増粘された硬化性成形材料およびその製造法
USRE30760E (en)	1981-10-06	Process for the production of synthetic resins containing isocyanurate groups
US20110015366A1 (en)	2011-01-20	Novel chain extenders for polyurethane elastomer formulations
KR890002401B1 (ko)	1989-07-03	파라핀 폴리올 및 이소시안에이트 반응성 프리폴리머를 함유하는 상안정성 조성물 및 그 제조방법
US5084544A (en)	1992-01-28	Cold setting reaction resin mixture and use thereof
JPS61502825A (ja)	1986-12-04	１級アミン化合物とポリエポキシドの末端２級アミン付加物を含有する活性水素含有組成物と，それから製造されるポリウレア含有ポリマ−
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JPH0826117B2 (ja)	1996-03-13	不飽和ビニルエステル樹脂組成物およびその増粘組成物
JP2633029B2 (ja)	1997-07-23	硬化型組成物
JPH03128916A (ja)	1991-05-31	熱硬化性の反応性樹脂組成物ならびに耐熱性成形品の製造方法
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JPH0352768B2 (ko)	1991-08-13
KR930005137B1 (ko)	1993-06-16	에폭시 수지용 경화제 조성물의 제조방법