TWI515215B - 聚唑烷酮樹脂 - Google Patents
聚唑烷酮樹脂 Download PDFInfo
- Publication number
- TWI515215B TWI515215B TW099138801A TW99138801A TWI515215B TW I515215 B TWI515215 B TW I515215B TW 099138801 A TW099138801 A TW 099138801A TW 99138801 A TW99138801 A TW 99138801A TW I515215 B TWI515215 B TW I515215B
- Authority
- TW
- Taiwan
- Prior art keywords
- epoxy
- resin composition
- functional group
- epoxy functional
- oxazolidinone
- Prior art date
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- 229920005989 resin Polymers 0.000 title description 47
- 239000011347 resin Substances 0.000 title description 47
- 239000000203 mixture Chemical group 0.000 claims description 112
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 97
- 239000004593 Epoxy Substances 0.000 claims description 86
- 229920000647 polyepoxide Polymers 0.000 claims description 79
- 239000003822 epoxy resin Substances 0.000 claims description 78
- 239000005056 polyisocyanate Substances 0.000 claims description 31
- 229920001228 polyisocyanate Polymers 0.000 claims description 31
- 125000000524 functional group Chemical group 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 229920001187 thermosetting polymer Polymers 0.000 claims description 25
- YDIZFUMZDHUHSH-UHFFFAOYSA-N 1,7-bis(ethenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical class C12OC2C=CC2(C=C)C1(C=C)O2 YDIZFUMZDHUHSH-UHFFFAOYSA-N 0.000 claims description 24
- -1 amine compound Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- 239000011342 resin composition Substances 0.000 claims 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 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 13
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 9
- 230000009477 glass transition Effects 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002841 Lewis acid Substances 0.000 claims description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 150000003839 salts Chemical group 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 3
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 3
- ILSRXKFYTXYKJS-UHFFFAOYSA-N 2,4-bis(ethenyl)-3,6-dioxatetracyclo[6.4.0.02,4.05,7]dodeca-1(12),8,10-triene Chemical class C=CC12OC1(C=C)C1=CC=CC=C1C1C2O1 ILSRXKFYTXYKJS-UHFFFAOYSA-N 0.000 claims description 2
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- PNZDZRMOBIIQTC-UHFFFAOYSA-N ethanamine;hydron;bromide Chemical compound Br.CCN PNZDZRMOBIIQTC-UHFFFAOYSA-N 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- LWOLJZRFQMSDAZ-UHFFFAOYSA-N syn-benzene dioxide Chemical compound C1=CC2OC2C2OC21 LWOLJZRFQMSDAZ-UHFFFAOYSA-N 0.000 claims 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 20
- 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 19
- 239000000126 substance Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 17
- 238000009472 formulation Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical class N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000005323 electroforming Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 229920001002 functional polymer Polymers 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 125000005496 phosphonium group Chemical group 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- UZXQULFXZDNGSO-UHFFFAOYSA-N 1-but-1-enyl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(C=CCC)C1O2 UZXQULFXZDNGSO-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- QFZKVFCEJRXRBD-UHFFFAOYSA-N 2-ethyl-4-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]-5-methyl-1h-imidazole Chemical compound N1C(CC)=NC(CC2=C(NC(CC)=N2)C)=C1C QFZKVFCEJRXRBD-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- GLPDXGJXUWGMQJ-UHFFFAOYSA-N 4-ethenyl-7-(4-ethenylphenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical compound C(=C)C1=CC=C(C=C1)C12C(C3C(C=C1)(C=C)O3)O2 GLPDXGJXUWGMQJ-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- RADFGVUHXFFJEL-UHFFFAOYSA-N [I-].[I-].[I-].[I-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [I-].[I-].[I-].[I-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 RADFGVUHXFFJEL-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
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- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GELSOTNVVKOYAW-UHFFFAOYSA-N ethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 GELSOTNVVKOYAW-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000004845 glycidylamine epoxy resin Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- MTCBLMPRPUTXHZ-UHFFFAOYSA-N n-(oxomethylidene)nitramide Chemical compound [O-][N+](=O)N=C=O MTCBLMPRPUTXHZ-UHFFFAOYSA-N 0.000 description 1
- AHNZVFVNAQKFBB-UHFFFAOYSA-N n-amino-n-(n-aminoanilino)aniline Chemical compound C=1C=CC=CC=1N(N)N(N)C1=CC=CC=C1 AHNZVFVNAQKFBB-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003573 thiols Chemical class 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
- 239000012745 toughening agent Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- UEWNEQVNIYYFFF-UHFFFAOYSA-N triphenylphosphanium;dibromide Chemical compound [Br-].[Br-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 UEWNEQVNIYYFFF-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C08G59/02—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
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
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)
- Polyurethanes Or Polyureas (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26066709P | 2009-11-12 | 2009-11-12 |
Publications (2)
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| TW201124437A TW201124437A (en) | 2011-07-16 |
| TWI515215B true TWI515215B (zh) | 2016-01-01 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099138801A TWI515215B (zh) | 2009-11-12 | 2010-11-11 | 聚唑烷酮樹脂 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8871892B2 (enExample) |
| EP (1) | EP2499180A2 (enExample) |
| JP (2) | JP5706437B2 (enExample) |
| KR (1) | KR20120097511A (enExample) |
| CN (2) | CN105713179A (enExample) |
| BR (1) | BR112012010870A2 (enExample) |
| TW (1) | TWI515215B (enExample) |
| WO (1) | WO2011059633A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2013005763A (es) | 2010-11-22 | 2013-06-18 | Dow Global Technologies Llc | Resina epoxica que comprende un aducto de dioxido de divinilbenceno como mejorador de la tenacidad. |
| US20140256909A1 (en) * | 2011-11-08 | 2014-09-11 | Dow Global Technologies Llc | Curable compositions |
| CN104271667B (zh) * | 2012-04-27 | 2018-01-26 | 陶氏环球技术有限责任公司 | 可固化环氧树脂组合物和由其制造的复合材料 |
| US9371417B2 (en) * | 2012-06-15 | 2016-06-21 | Blue Cube Ip Llc | Curable compositions |
| CN104768998B (zh) * | 2012-10-01 | 2016-10-12 | 陶氏环球技术有限公司 | 可固化环氧树脂组合物 |
| CN104736592A (zh) * | 2012-10-17 | 2015-06-24 | 陶氏环球技术有限公司 | 用于高温应用的韧化、可固化的环氧组合物 |
| BR112015010248A2 (pt) * | 2012-11-07 | 2017-07-11 | Dow Global Technologies Llc | composição de resina epóxi curável, processo para preparar a composição de resina epóxi curável e compósito |
| CN105452321A (zh) * | 2013-08-16 | 2016-03-30 | 陶氏环球技术有限责任公司 | 1k热固性环氧树脂组合物 |
| CN103834168B (zh) | 2014-02-25 | 2016-09-07 | 广东生益科技股份有限公司 | 一种无卤阻燃型树脂组合物 |
| CN106459358B (zh) * | 2014-05-12 | 2020-05-15 | 科思创德国股份有限公司 | 用于生产聚噁唑烷酮聚合物化合物的方法 |
| DE102014226842A1 (de) | 2014-12-22 | 2016-06-23 | Henkel Ag & Co. Kgaa | Katalysator-Zusammensetzung zur Härtung von Epoxidgruppen-haltigen Harzen |
| DE102014226838A1 (de) * | 2014-12-22 | 2016-06-23 | Henkel Ag & Co. Kgaa | Oxazolidinon- und Isocyanurat-vernetzte Matrix für faserverstärktes Material |
| CN105778414B (zh) | 2014-12-26 | 2018-05-29 | 广东生益科技股份有限公司 | 一种环氧树脂组合物以及使用它的预浸料和层压板 |
| ES2731925T3 (es) * | 2015-02-13 | 2019-11-19 | Covestro Deutschland Ag | Procedimiento para la síntesis de compuestos de polioxazolidinona con alta estabilidad |
| CN106916282B (zh) | 2015-12-28 | 2019-07-26 | 广东生益科技股份有限公司 | 一种环氧树脂组合物以及使用其的预浸料和层压板 |
| CN106519185B (zh) * | 2016-11-16 | 2020-03-31 | 苏州太湖电工新材料股份有限公司 | 一种聚噁唑烷酮树脂、其制备方法及在绝缘漆中的应用 |
| ES2908680T3 (es) * | 2017-03-17 | 2022-05-03 | Basf Se | Proceso para la preparación de compuestos con grupos oxazolidinona |
| JP7365096B2 (ja) * | 2017-09-29 | 2023-10-19 | ビーエーエスエフ ソシエタス・ヨーロピア | ジイソシアネートおよび２－フェニル－１，３－プロパンジオールのジグリシジルエーテル誘導体からの熱可塑性ポリオキサゾリドン |
| ES3013876T3 (en) * | 2018-05-18 | 2025-04-15 | Dow Global Technologies Llc | A polyisocyanate component, a polyurethane foaming system and an article made therefrom |
| JP7512249B2 (ja) * | 2018-07-18 | 2024-07-08 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリオキサゾリドンのバルク重合 |
| US20210261715A1 (en) * | 2018-07-30 | 2021-08-26 | Dow Global Technologies Llc | Curable resin composition |
| EP3640276A1 (en) * | 2018-10-16 | 2020-04-22 | SABIC Global Technologies B.V. | High heat epoxy-terminated polyoxazolidones, compositions, methods of manufacture, and uses thereof |
| EP3647335A1 (en) * | 2018-10-30 | 2020-05-06 | Covestro Deutschland AG | Method for the production of thermoplastic polyoxazolidinone polymers |
| KR102510064B1 (ko) | 2021-06-03 | 2023-03-14 | 한국화학연구원 | 지속 가능한 자원과 이산화탄소를 이용한 폴리옥사졸리돈의 제조방법, 이를 이용하여 제조된 폴리옥사졸리돈 및 이를 포함하는 성형체 |
| CN118308011A (zh) * | 2024-05-14 | 2024-07-09 | 络合高新材料(上海)有限公司 | 一种高延伸率石油管道修补涂料环氧树脂组合物 |
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| US3198851A (en) * | 1961-02-23 | 1965-08-03 | Union Carbide Corp | Polyurethanes from non-hydroxyl polyepoxides, bf3-amine catalyst and alternatively avinyl chloride containing resin |
| US3242108A (en) * | 1961-04-04 | 1966-03-22 | Union Carbide Corp | Compositions for producing polyurethane resins and resinous foams and products prepared therefrom |
| US3313747A (en) | 1964-10-29 | 1967-04-11 | Baker Chem Co J T | Polymers prepared from isocyanateoxazolidinones |
| US3334110A (en) * | 1965-08-16 | 1967-08-01 | Baker Chem Co J T | Method for preparing epoxyoxazolidinones |
| US3737406A (en) | 1971-03-22 | 1973-06-05 | Alelio G D | Reactive epoxy-onium catalysts for synthesis of polyoxazolidones |
| US4066628A (en) | 1976-08-02 | 1978-01-03 | Mitsubishi Chemical Industries Ltd. | Oxazolidone catalyst |
| ZA839459B (en) * | 1982-12-30 | 1985-08-28 | Mobil Oil Corp | Polyoxazolidone powder coating compositions |
| US4658007A (en) * | 1985-05-07 | 1987-04-14 | The Dow Chemical Company | Polyisocyanurate-based polyoxazolidone polymers and process for their preparation |
| US5917707A (en) | 1993-11-16 | 1999-06-29 | Formfactor, Inc. | Flexible contact structure with an electrically conductive shell |
| US4742146A (en) | 1985-10-18 | 1988-05-03 | The Dow Chemical Company | Urethane modified epoxy resin compositions containing oxazolidinone or thiazolidinone groups |
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| GB8912952D0 (en) * | 1989-06-06 | 1989-07-26 | Dow Rheinmuenster | Epoxy-terminated polyoxazolidones,process for the preparation thereof and electrical laminates made from the epoxy-terminated polyoxazolidones |
| DE69133280T2 (de) * | 1990-05-21 | 2004-05-06 | Dow Global Technologies, Inc., Midland | Latente Katalysatoren, Härtungsinhibierte Epoxyharzzusammensetzungen und daraus hergestellte Laminate |
| US5135993A (en) | 1990-09-11 | 1992-08-04 | Dow Corning Corporation | High modulus silicones as toughening agents for epoxy resins |
| GB9411367D0 (en) | 1994-06-07 | 1994-07-27 | Ici Composites Inc | Curable Composites |
| US6153719A (en) | 1998-02-04 | 2000-11-28 | Lord Corporation | Thiol-cured epoxy composition |
| GB9817799D0 (en) * | 1998-08-14 | 1998-10-14 | Dow Deutschland Inc | Viscosity modifier for thermosetting resin compositioning |
| JP2000128959A (ja) | 1998-10-27 | 2000-05-09 | Nippon Paint Co Ltd | オキサゾリドン環含有エポキシ樹脂 |
| GB9827367D0 (en) * | 1998-12-11 | 1999-02-03 | Dow Deutschland Inc | Adhesive resin composition |
| US6632893B2 (en) | 1999-05-28 | 2003-10-14 | Henkel Loctite Corporation | Composition of epoxy resin, cyanate ester, imidazole and polysulfide tougheners |
| US6572971B2 (en) | 2001-02-26 | 2003-06-03 | Ashland Chemical | Structural modified epoxy adhesive compositions |
| US6632860B1 (en) | 2001-08-24 | 2003-10-14 | Texas Research International, Inc. | Coating with primer and topcoat both containing polysulfide, epoxy resin and rubber toughener |
| GB0212062D0 (en) | 2002-05-24 | 2002-07-03 | Vantico Ag | Jetable compositions |
| US7163973B2 (en) | 2002-08-08 | 2007-01-16 | Henkel Corporation | Composition of bulk filler and epoxy-clay nanocomposite |
| US6887574B2 (en) | 2003-06-06 | 2005-05-03 | Dow Global Technologies Inc. | Curable flame retardant epoxy compositions |
| CN102653598B (zh) | 2004-05-28 | 2015-05-13 | 陶氏环球技术有限责任公司 | 可用于制造无卤素抗引燃聚合物的含磷化合物 |
| BRPI0516702A (pt) | 2004-11-10 | 2008-09-16 | Dow Global Technologies Inc | composição de verniz de resina epóxi para laminados curável, processo para preparar uma composição de verniz para laminados de resina epóxi curável, processo para preparar um laminado, laminado e pré-impregnado |
| EP1867672B1 (en) * | 2005-04-07 | 2011-01-26 | Asahi Kasei Chemicals Corporation | Epoxy resin composition |
| US8048819B2 (en) | 2005-06-23 | 2011-11-01 | Momentive Performance Materials Inc. | Cure catalyst, composition, electronic device and associated method |
| CN101815734A (zh) * | 2007-10-05 | 2010-08-25 | 陶氏环球技术公司 | 异氰酸酯改性环氧树脂及其环氧粉末涂料组合物 |
| TW200922959A (en) * | 2007-10-26 | 2009-06-01 | Dow Global Technologies Inc | Epoxy resin composition containing isocyanurates for use in electrical laminates |
| BRPI0817181A8 (pt) * | 2007-10-31 | 2016-12-20 | Dow Global Technologies Inc | Polímero termofixo contendo anel de oxazolidinona terminado por epóxi, composição termofixa de revestimento em pó, substrato, método para prover um substrato com um revestimento epóxi ligado por fusão (fbe), substrato revestido, método para preparar um polimero contendo um anel de oxazolidinona terminado por epóxi e polímero |
-
2010
- 2010-10-15 KR KR1020127015002A patent/KR20120097511A/ko not_active Ceased
- 2010-10-15 WO PCT/US2010/052767 patent/WO2011059633A2/en not_active Ceased
- 2010-10-15 US US13/498,709 patent/US8871892B2/en not_active Expired - Fee Related
- 2010-10-15 EP EP10768164A patent/EP2499180A2/en not_active Withdrawn
- 2010-10-15 JP JP2012538829A patent/JP5706437B2/ja not_active Expired - Fee Related
- 2010-10-15 BR BR112012010870A patent/BR112012010870A2/pt not_active IP Right Cessation
- 2010-10-15 CN CN201610034163.0A patent/CN105713179A/zh active Pending
- 2010-10-15 CN CN201080051377.XA patent/CN102666633B/zh not_active Expired - Fee Related
- 2010-11-11 TW TW099138801A patent/TWI515215B/zh not_active IP Right Cessation
-
2014
- 2014-12-05 JP JP2014246774A patent/JP6073284B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN102666633A (zh) | 2012-09-12 |
| BR112012010870A2 (pt) | 2019-09-24 |
| EP2499180A2 (en) | 2012-09-19 |
| CN102666633B (zh) | 2016-02-17 |
| US8871892B2 (en) | 2014-10-28 |
| TW201124437A (en) | 2011-07-16 |
| JP2013510924A (ja) | 2013-03-28 |
| WO2011059633A2 (en) | 2011-05-19 |
| US20120214958A1 (en) | 2012-08-23 |
| KR20120097511A (ko) | 2012-09-04 |
| WO2011059633A3 (en) | 2011-09-29 |
| JP6073284B2 (ja) | 2017-02-01 |
| JP2015061925A (ja) | 2015-04-02 |
| JP5706437B2 (ja) | 2015-04-22 |
| CN105713179A (zh) | 2016-06-29 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |