SG181461A1 - Epoxy resin compositions - Google Patents
Epoxy resin compositions Download PDFInfo
- Publication number
- SG181461A1 SG181461A1 SG2012040291A SG2012040291A SG181461A1 SG 181461 A1 SG181461 A1 SG 181461A1 SG 2012040291 A SG2012040291 A SG 2012040291A SG 2012040291 A SG2012040291 A SG 2012040291A SG 181461 A1 SG181461 A1 SG 181461A1
- Authority
- SG
- Singapore
- Prior art keywords
- formula
- epoxy resin
- resin composition
- substituted
- advanced
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 165
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 158
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 156
- -1 cycloalkane compound Chemical class 0.000 claims abstract description 32
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000843 powder Substances 0.000 claims abstract description 14
- 229930185605 Bisphenol Natural products 0.000 claims description 64
- 239000011342 resin composition Substances 0.000 claims description 55
- 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 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 22
- 239000004593 Epoxy Substances 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000002118 epoxides Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000007812 deficiency Effects 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000008199 coating composition Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 13
- 239000002131 composite material Substances 0.000 abstract description 8
- 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 118
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 87
- 229920005989 resin Polymers 0.000 description 81
- 239000011347 resin Substances 0.000 description 81
- 229920001187 thermosetting polymer Polymers 0.000 description 34
- 229940106691 bisphenol a Drugs 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 27
- 229920003986 novolac Polymers 0.000 description 27
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 239000000654 additive Substances 0.000 description 18
- 239000004634 thermosetting polymer Substances 0.000 description 18
- 239000011521 glass Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 12
- 230000009477 glass transition Effects 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000945 filler Substances 0.000 description 11
- 239000004848 polyfunctional curative Substances 0.000 description 11
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000005266 casting Methods 0.000 description 9
- 235000013824 polyphenols Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 238000009472 formulation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000004448 titration Methods 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 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 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000005538 encapsulation Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 description 4
- 238000004382 potting Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- AGBWDHTZUCGTAI-UHFFFAOYSA-N 1-(cycloundecen-1-yl)-3-diazocycloundecene Chemical compound [N-]=[N+]=C1CCCCCCCCC(C=2CCCCCCCCCC=2)=C1 AGBWDHTZUCGTAI-UHFFFAOYSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- SXOZDDAFVJANJP-UHFFFAOYSA-N cyclodecanone Chemical compound O=C1CCCCCCCCC1 SXOZDDAFVJANJP-UHFFFAOYSA-N 0.000 description 3
- NPEJHLDODKUWCF-UHFFFAOYSA-N cycloicosanone Chemical compound O=C1CCCCCCCCCCCCCCCCCCC1 NPEJHLDODKUWCF-UHFFFAOYSA-N 0.000 description 3
- WXAYGJXNCLBUDJ-UHFFFAOYSA-N cyclooctadecanone Chemical compound O=C1CCCCCCCCCCCCCCCCC1 WXAYGJXNCLBUDJ-UHFFFAOYSA-N 0.000 description 3
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000002787 reinforcement Effects 0.000 description 3
- 150000003335 secondary amines Chemical group 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RJWLXGOSIRVRAR-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C(C)=C1O RJWLXGOSIRVRAR-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- OLJXRTRRJSMURJ-UHFFFAOYSA-N 4-amino-2-methoxybenzoic acid Chemical compound COC1=CC(N)=CC=C1C(O)=O OLJXRTRRJSMURJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZVIDMSBTYRSMAR-UHFFFAOYSA-N N-Methyl-4-aminobenzoate Chemical compound CNC1=CC=C(C(O)=O)C=C1 ZVIDMSBTYRSMAR-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- XOSYHSRXLVMOBA-UHFFFAOYSA-N cyclopenta-1,3-diene;phenol Chemical compound C1C=CC=C1.C1C=CC=C1.OC1=CC=CC=C1 XOSYHSRXLVMOBA-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 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
- 239000000975 dye Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 210000003739 neck Anatomy 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 125000005592 polycycloalkyl group Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- ZLUJJCPTVKQVDE-UHFFFAOYSA-N (4-aminophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(O)C=C1 ZLUJJCPTVKQVDE-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- SATBYUZLZBFXED-UHFFFAOYSA-N (4-aminophenyl)methanone Chemical compound NC1=CC=C([C+]=O)C=C1 SATBYUZLZBFXED-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
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- 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
-
- 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
-
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26579909P | 2009-12-02 | 2009-12-02 | |
| PCT/US2010/056102 WO2011068644A1 (en) | 2009-12-02 | 2010-11-10 | Epoxy resin compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG181461A1 true SG181461A1 (en) | 2012-07-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012040291A SG181461A1 (en) | 2009-12-02 | 2010-11-10 | Epoxy resin compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8937145B2 (https=) |
| EP (1) | EP2507283B1 (https=) |
| JP (1) | JP2013512988A (https=) |
| KR (1) | KR20120101096A (https=) |
| CN (1) | CN102648227B (https=) |
| SG (1) | SG181461A1 (https=) |
| TW (1) | TWI488879B (https=) |
| WO (1) | WO2011068644A1 (https=) |
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| EP2507285A2 (en) * | 2009-12-02 | 2012-10-10 | Dow Global Technologies LLC | Composite compositions |
| SG181486A1 (en) | 2009-12-02 | 2012-07-30 | Dow Global Technologies Llc | Coating compositions |
| WO2011068644A1 (en) | 2009-12-02 | 2011-06-09 | Dow Global Technologies Inc. | Epoxy resin compositions |
| EP2558543B1 (en) | 2010-04-16 | 2017-08-30 | Valspar Sourcing, Inc. | Coating compositions for packaging articles and methods of coating |
| KR20130073906A (ko) | 2010-04-29 | 2013-07-03 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리시클로펜타디엔 폴리페놀의 폴리(알릴 에테르) |
| CN102971282B (zh) | 2010-04-29 | 2015-11-25 | 陶氏环球技术有限责任公司 | 聚环戊二烯多酚和聚氰酸酯聚环戊二烯多酚化合物 |
| WO2011136845A1 (en) | 2010-04-29 | 2011-11-03 | Dow Global Technologies Llc | Vinylbenzyl ethers of polycyclopentadiene polyphenol |
| EP3878912B1 (en) | 2011-02-07 | 2023-04-05 | Swimc Llc | Coating compositions for containers and other articles and methods of coating |
| US9139690B2 (en) | 2011-04-27 | 2015-09-22 | University Of Massachusetts Lowell | Bisphenol A (BPA) free epoxy resins |
| US20120328811A1 (en) * | 2011-06-24 | 2012-12-27 | Air Products And Chemicals, Inc. | Epoxy Resin Compositions |
| US9309381B2 (en) | 2011-06-24 | 2016-04-12 | Air Products And Chemicals, Inc. | Epoxy resin compositions using solvated solids |
| BR112014018939B1 (pt) * | 2012-02-24 | 2021-02-23 | Dow Global Technologies Llc | Poliglicidil éteres, métodos para preparar os compostos, composiçõescuradas e adutos |
| JP6166286B2 (ja) | 2012-02-24 | 2017-07-19 | ダウ グローバル テクノロジーズ エルエルシー | シクロドデカンポリフェノールのポリシアナートおよびその熱硬化性樹脂 |
| JP2013253153A (ja) * | 2012-06-06 | 2013-12-19 | Mitsubishi Chemicals Corp | エポキシ樹脂、エポキシ樹脂組成物、硬化物及び光学部材 |
| JP2014034629A (ja) * | 2012-08-08 | 2014-02-24 | Mitsubishi Chemicals Corp | エポキシ樹脂組成物、硬化物及び半導体封止材 |
| AU2013299578A1 (en) | 2012-08-09 | 2015-02-19 | Valspar Sourcing, Inc. | Compositions for containers and other articles and methods of using same |
| CN102911585B (zh) * | 2012-09-28 | 2015-09-30 | 广州擎天材料科技有限公司 | 一种中高档汽车铝轮毂专用底粉涂料及其制备方法 |
| WO2014186279A1 (en) | 2013-05-13 | 2014-11-20 | Momentive Specialty Chem Inc | Composites and epoxy resins based on aryl substituted compounds |
| US10662304B2 (en) | 2013-12-31 | 2020-05-26 | Saint-Gobain Performance Plastics Corporation | Composites for protecting signal transmitters/receivers |
| CN110790914A (zh) | 2014-04-14 | 2020-02-14 | 宣伟投资管理有限公司 | 制备用于容器和其它制品的组合物的方法以及使用所述组合物的方法 |
| JP6452133B2 (ja) * | 2015-02-17 | 2019-01-16 | 田岡化学工業株式会社 | 環状炭化水素骨格を有するエポキシ樹脂 |
| TWI614275B (zh) | 2015-11-03 | 2018-02-11 | Valspar Sourcing Inc | 用於製備聚合物的液體環氧樹脂組合物 |
| SG11201900686XA (en) * | 2016-07-25 | 2019-02-27 | Isola Usa Corp | Improved sma resin formulation |
| CN113861383B (zh) * | 2021-10-19 | 2024-04-19 | 上海华谊树脂有限公司 | 含萘环结构的环氧树脂及其制备方法 |
| CN113929871B (zh) * | 2021-11-05 | 2022-09-02 | 白银图微新材料科技有限公司 | 一种聚硫酸酯型环氧树脂的制备方法 |
| CN116554128B (zh) * | 2023-05-08 | 2025-09-05 | 四川大学 | 一种自固化、高模高强的本征阻燃磺胺环氧树脂及其制备方法 |
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| SG181486A1 (en) * | 2009-12-02 | 2012-07-30 | Dow Global Technologies Llc | Coating compositions |
| WO2011068644A1 (en) | 2009-12-02 | 2011-06-09 | Dow Global Technologies Inc. | Epoxy resin compositions |
| EP2507285A2 (en) * | 2009-12-02 | 2012-10-10 | Dow Global Technologies LLC | Composite compositions |
-
2010
- 2010-11-10 WO PCT/US2010/056102 patent/WO2011068644A1/en not_active Ceased
- 2010-11-10 EP EP10778810.1A patent/EP2507283B1/en not_active Not-in-force
- 2010-11-10 SG SG2012040291A patent/SG181461A1/en unknown
- 2010-11-10 CN CN201080054831.7A patent/CN102648227B/zh active Active
- 2010-11-10 KR KR1020127016913A patent/KR20120101096A/ko not_active Ceased
- 2010-11-10 JP JP2012542034A patent/JP2013512988A/ja active Pending
- 2010-11-10 US US13/512,705 patent/US8937145B2/en active Active
- 2010-12-01 TW TW099141671A patent/TWI488879B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW201136971A (en) | 2011-11-01 |
| JP2013512988A (ja) | 2013-04-18 |
| WO2011068644A1 (en) | 2011-06-09 |
| KR20120101096A (ko) | 2012-09-12 |
| CN102648227B (zh) | 2015-08-26 |
| TWI488879B (zh) | 2015-06-21 |
| EP2507283B1 (en) | 2013-10-23 |
| EP2507283A1 (en) | 2012-10-10 |
| CN102648227A (zh) | 2012-08-22 |
| US8937145B2 (en) | 2015-01-20 |
| US20120238709A1 (en) | 2012-09-20 |
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