JP2013512988A - エポキシ樹脂組成物 - Google Patents
エポキシ樹脂組成物 Download PDFInfo
- Publication number
- JP2013512988A JP2013512988A JP2012542034A JP2012542034A JP2013512988A JP 2013512988 A JP2013512988 A JP 2013512988A JP 2012542034 A JP2012542034 A JP 2012542034A JP 2012542034 A JP2012542034 A JP 2012542034A JP 2013512988 A JP2013512988 A JP 2013512988A
- Authority
- JP
- Japan
- Prior art keywords
- resin composition
- epoxy resin
- group
- formula
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 178
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 169
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 169
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000843 powder Substances 0.000 claims abstract description 15
- 229920001187 thermosetting polymer Polymers 0.000 claims description 103
- 239000011342 resin composition Substances 0.000 claims description 63
- 229930185605 Bisphenol Natural products 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 41
- 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 41
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- -1 bisphenol compound Chemical class 0.000 claims description 32
- 239000004593 Epoxy Substances 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000002118 epoxides Chemical group 0.000 claims description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 230000002950 deficient Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 12
- 239000002131 composite material Substances 0.000 abstract description 8
- 229920005989 resin Polymers 0.000 description 129
- 239000011347 resin Substances 0.000 description 129
- 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 111
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 82
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 32
- 229940106691 bisphenol a Drugs 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
- 229920003986 novolac Polymers 0.000 description 27
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000654 additive Substances 0.000 description 18
- 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 16
- 239000011521 glass Substances 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000000113 differential scanning calorimetry Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000945 filler Substances 0.000 description 11
- 230000009477 glass transition Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000004634 thermosetting polymer Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000005022 packaging material Substances 0.000 description 8
- 235000013824 polyphenols Nutrition 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- 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 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
- 125000000743 hydrocarbylene group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 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 4
- 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
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 239000011248 coating agent Substances 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 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
- 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
- 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 3
- 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 compound 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 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 238000004382 potting Methods 0.000 description 3
- 238000012545 processing Methods 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
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-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
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 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
- 229920000147 Styrene maleic anhydride Polymers 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
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 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
- 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
- 150000001491 aromatic compounds Chemical class 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- NNSXQVFLSINZGU-UHFFFAOYSA-N cyclododecanone;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.O=C1CCCCCCCCCCC1 NNSXQVFLSINZGU-UHFFFAOYSA-N 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
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 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
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000004845 glycidylamine epoxy resin Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000004615 ingredient 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- 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
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 150000003003 phosphines 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
- 229920000642 polymer Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012779 reinforcing material 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
- 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
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 230000004580 weight loss Effects 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
- 125000004209 (C1-C8) alkyl group Chemical group 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
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical class CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- KCVHYRQVGPQSRV-UHFFFAOYSA-N 1-n,4-n-bis(4-hydroxyphenyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(O)=CC=2)C=C1 KCVHYRQVGPQSRV-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RNPYLDOBLOBMDH-UHFFFAOYSA-N 10,10-diphenylcyclooctadecane-1,1-diol Chemical compound OC1(CCCCCCCCC(CCCCCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1)O RNPYLDOBLOBMDH-UHFFFAOYSA-N 0.000 description 1
- KVWOUQJTLNNASQ-UHFFFAOYSA-N 11,11-diphenylcycloicosane-1,1-diol Chemical compound OC1(CCCCCCCCCC(CCCCCCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1)O KVWOUQJTLNNASQ-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FAPHVFZJTOJMJT-UHFFFAOYSA-N 2,2-dihydroxy-6,6-diphenylcyclodecan-1-one Chemical compound OC1(C(CCCCC(CCC1)(C1=CC=CC=C1)C1=CC=CC=C1)=O)O FAPHVFZJTOJMJT-UHFFFAOYSA-N 0.000 description 1
- OUBGWYBRTFVADX-UHFFFAOYSA-N 2,2-dimethyl-8,8-diphenylcyclododecane-1,1-diol Chemical compound OC1(C(CCCCCC(CCCC1)(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)O OUBGWYBRTFVADX-UHFFFAOYSA-N 0.000 description 1
- VUNSKHOMYKIXOR-UHFFFAOYSA-N 2,2-diphenylcyclononane-1,1-diol Chemical compound OC1(O)CCCCCCCC1(C=1C=CC=CC=1)C1=CC=CC=C1 VUNSKHOMYKIXOR-UHFFFAOYSA-N 0.000 description 1
- HRTKKTVXDSRMEC-UHFFFAOYSA-N 2,2-diphenylcyclopentadecane-1,1-diol Chemical compound OC1(O)CCCCCCCCCCCCCC1(C=1C=CC=CC=1)C1=CC=CC=C1 HRTKKTVXDSRMEC-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- ZEBMBNNVUIWRIC-UHFFFAOYSA-N 2,6-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(C)=C1S(N)(=O)=O ZEBMBNNVUIWRIC-UHFFFAOYSA-N 0.000 description 1
- MYEWQUYMRFSJHT-UHFFFAOYSA-N 2-(2-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1N MYEWQUYMRFSJHT-UHFFFAOYSA-N 0.000 description 1
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 1
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 description 1
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
- BMALTXIIHBBMPO-UHFFFAOYSA-N 2-[bis(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1C(C=1C(=CC=CC=1)N)C1=CC=CC=C1N BMALTXIIHBBMPO-UHFFFAOYSA-N 0.000 description 1
- OAYOHLUHNUECAZ-UHFFFAOYSA-N 2-[bis(2-carboxyphenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(C=1C(=CC=CC=1)C(O)=O)C1=CC=CC=C1C(O)=O OAYOHLUHNUECAZ-UHFFFAOYSA-N 0.000 description 1
- FHYOJDLWRUYQSN-UHFFFAOYSA-N 2-[bis(2-sulfanylphenyl)methyl]benzenethiol Chemical compound SC1=CC=CC=C1C(C=1C(=CC=CC=1)S)C1=CC=CC=C1S FHYOJDLWRUYQSN-UHFFFAOYSA-N 0.000 description 1
- YWIHGHOTVHUWJN-UHFFFAOYSA-N 2-aminoacetic acid;2-(methylamino)acetic acid Chemical compound NCC(O)=O.CNCC(O)=O YWIHGHOTVHUWJN-UHFFFAOYSA-N 0.000 description 1
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-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
- MCWQZEPQUWFZST-UHFFFAOYSA-N 3,3,4,4-tetrabromo-2,2-diphenylcyclododecane-1,1-diol Chemical compound OC1(O)CCCCCCCCC(Br)(Br)C(Br)(Br)C1(C=1C=CC=CC=1)C1=CC=CC=C1 MCWQZEPQUWFZST-UHFFFAOYSA-N 0.000 description 1
- SLWNDROCBOWRLG-UHFFFAOYSA-N 3,3-dibromo-9,9-dimethyl-2,2-diphenylcyclododecane-1,1-diol Chemical compound OC1(C(C(CCCCCC(CCC1)(C)C)(Br)Br)(C1=CC=CC=C1)C1=CC=CC=C1)O SLWNDROCBOWRLG-UHFFFAOYSA-N 0.000 description 1
- LIEAZDIMPFTVCL-UHFFFAOYSA-N 3,5-dibromo-4-[2-(6,6-dibromo-4-hydroxycyclohexa-1,3-dien-1-yl)propan-2-yl]phenol Chemical compound BrC=1C=C(O)C=C(Br)C=1C(C)(C)C1=CC=C(O)CC1(Br)Br LIEAZDIMPFTVCL-UHFFFAOYSA-N 0.000 description 1
- RIESCGNDMPQMRK-UHFFFAOYSA-N 3,5-dichloro-4-[2-(6,6-dichloro-4-hydroxycyclohexa-1,3-dien-1-yl)propan-2-yl]phenol Chemical compound ClC=1C=C(O)C=C(Cl)C=1C(C)(C)C1=CC=C(O)CC1(Cl)Cl RIESCGNDMPQMRK-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 description 1
- QPIOXOJERGNNMX-UHFFFAOYSA-N 3-(3-aminopropylsulfanyl)propan-1-amine Chemical compound NCCCSCCCN QPIOXOJERGNNMX-UHFFFAOYSA-N 0.000 description 1
- JPVKCHIPRSQDKL-UHFFFAOYSA-N 3-aminobenzenesulfonamide Chemical compound NC1=CC=CC(S(N)(=O)=O)=C1 JPVKCHIPRSQDKL-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- ODJNLCWKJIOCHS-UHFFFAOYSA-N 4-(1-phenylprop-1-en-2-yl)aniline Chemical compound C=1C=C(N)C=CC=1C(C)=CC1=CC=CC=C1 ODJNLCWKJIOCHS-UHFFFAOYSA-N 0.000 description 1
- OBEQANYTGDITJM-UHFFFAOYSA-N 4-(4-aminobenzoyl)benzoic acid Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 OBEQANYTGDITJM-UHFFFAOYSA-N 0.000 description 1
- DVFCGSZRLJQHJA-UHFFFAOYSA-N 4-(4-aminophenoxy)benzoic acid Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(O)=O)C=C1 DVFCGSZRLJQHJA-UHFFFAOYSA-N 0.000 description 1
- GLZLLFXFYSNLKA-UHFFFAOYSA-N 4-(4-aminophenoxy)phenol Chemical compound C1=CC(N)=CC=C1OC1=CC=C(O)C=C1 GLZLLFXFYSNLKA-UHFFFAOYSA-N 0.000 description 1
- XRLMLNFQXZPRKQ-UHFFFAOYSA-N 4-(4-aminophenyl)sulfanylbenzoic acid Chemical compound C1=CC(N)=CC=C1SC1=CC=C(C(O)=O)C=C1 XRLMLNFQXZPRKQ-UHFFFAOYSA-N 0.000 description 1
- CCIRXAPQORDYNX-UHFFFAOYSA-N 4-(4-aminophenyl)sulfanylphenol Chemical compound C1=CC(N)=CC=C1SC1=CC=C(O)C=C1 CCIRXAPQORDYNX-UHFFFAOYSA-N 0.000 description 1
- ANJUQZCKLXYDJX-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonylbenzoic acid Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 ANJUQZCKLXYDJX-UHFFFAOYSA-N 0.000 description 1
- PSHPCZGANRRQDN-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonylphenol Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 PSHPCZGANRRQDN-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- OZUBMBIDHPBIDL-UHFFFAOYSA-N 4-Propylcyclohexylamine Chemical compound CCCC1CCC(N)CC1 OZUBMBIDHPBIDL-UHFFFAOYSA-N 0.000 description 1
- XGKGITBBMXTKTE-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)disulfanyl]phenol Chemical compound C1=CC(O)=CC=C1SSC1=CC=C(O)C=C1 XGKGITBBMXTKTE-UHFFFAOYSA-N 0.000 description 1
- RYXFMCKXOQMCSM-UHFFFAOYSA-N 4-[(4-sulfanylphenyl)methyl]benzenethiol Chemical compound C1=CC(S)=CC=C1CC1=CC=C(S)C=C1 RYXFMCKXOQMCSM-UHFFFAOYSA-N 0.000 description 1
- KOGDFDWINXIWHI-OWOJBTEDSA-N 4-[(e)-2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1 KOGDFDWINXIWHI-OWOJBTEDSA-N 0.000 description 1
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 1
- PMNXCGMIMVLCRP-ZHACJKMWSA-N 4-[(e)-2-(4-hydroxyphenyl)prop-1-enyl]phenol Chemical compound C=1C=C(O)C=CC=1C(/C)=C/C1=CC=C(O)C=C1 PMNXCGMIMVLCRP-ZHACJKMWSA-N 0.000 description 1
- CHIJEKAVDZLCJA-OWOJBTEDSA-N 4-[(e)-2-(4-nitrophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1 CHIJEKAVDZLCJA-OWOJBTEDSA-N 0.000 description 1
- VFPLSXYJYAKZCT-VOTSOKGWSA-N 4-[(e)-2-phenylethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=CC=C1 VFPLSXYJYAKZCT-VOTSOKGWSA-N 0.000 description 1
- ZSQIQUAKDNTQOI-UHFFFAOYSA-N 4-[1-(4-aminophenyl)cyclohexyl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)CCCCC1 ZSQIQUAKDNTQOI-UHFFFAOYSA-N 0.000 description 1
- KGUPCCIBHWPJBT-UHFFFAOYSA-N 4-[1-(4-aminophenyl)ethyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)C1=CC=C(N)C=C1 KGUPCCIBHWPJBT-UHFFFAOYSA-N 0.000 description 1
- SXPHLVPUKPVLMA-UHFFFAOYSA-N 4-[1-(4-aminophenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(N)C=C1 SXPHLVPUKPVLMA-UHFFFAOYSA-N 0.000 description 1
- XXUYRHRBCAATNM-UHFFFAOYSA-N 4-[1-(4-aminophenyl)prop-1-en-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)=CC1=CC=C(N)C=C1 XXUYRHRBCAATNM-UHFFFAOYSA-N 0.000 description 1
- GNFUZCCCNCUWMN-UHFFFAOYSA-N 4-[1-(4-aminophenyl)prop-1-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)=CC1=CC=C(N)C=C1 GNFUZCCCNCUWMN-UHFFFAOYSA-N 0.000 description 1
- HNRCCLURCMAHHA-UHFFFAOYSA-N 4-[1-(4-carboxyphenyl)cyclohexyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1(C=2C=CC(=CC=2)C(O)=O)CCCCC1 HNRCCLURCMAHHA-UHFFFAOYSA-N 0.000 description 1
- XJGAWOUZDSIZIA-UHFFFAOYSA-N 4-[1-(4-sulfanylphenyl)cyclohexyl]benzenethiol Chemical compound C1=CC(S)=CC=C1C1(C=2C=CC(S)=CC=2)CCCCC1 XJGAWOUZDSIZIA-UHFFFAOYSA-N 0.000 description 1
- RMUKVWGPYSCWQA-UHFFFAOYSA-N 4-[2-(3-aminophenyl)propan-2-yl]phenol Chemical compound C=1C=CC(N)=CC=1C(C)(C)C1=CC=C(O)C=C1 RMUKVWGPYSCWQA-UHFFFAOYSA-N 0.000 description 1
- RTTWZUMYDDOVHT-UHFFFAOYSA-N 4-[2-(4-aminophenyl)prop-1-enyl]benzoic acid Chemical compound C=1C=C(N)C=CC=1C(C)=CC1=CC=C(C(O)=O)C=C1 RTTWZUMYDDOVHT-UHFFFAOYSA-N 0.000 description 1
- UUSKOXFQQXSBBT-UHFFFAOYSA-N 4-[2-(4-aminophenyl)prop-1-enyl]phenol Chemical compound C=1C=C(N)C=CC=1C(C)=CC1=CC=C(O)C=C1 UUSKOXFQQXSBBT-UHFFFAOYSA-N 0.000 description 1
- QNXSCGOTCOMDQD-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)prop-1-enyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)=CC1=CC=C(C(O)=O)C=C1 QNXSCGOTCOMDQD-UHFFFAOYSA-N 0.000 description 1
- NOAJUPSZEXJONN-UHFFFAOYSA-N 4-[2-(4-hydroxy-2-methoxyphenyl)propan-2-yl]-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1OC NOAJUPSZEXJONN-UHFFFAOYSA-N 0.000 description 1
- DYLPULNBWUCSPQ-UHFFFAOYSA-N 4-[2-(4-sulfanylphenyl)prop-1-enyl]benzenethiol Chemical compound C=1C=C(S)C=CC=1C(C)=CC1=CC=C(S)C=C1 DYLPULNBWUCSPQ-UHFFFAOYSA-N 0.000 description 1
- WRKHXTXBQDPSEH-UHFFFAOYSA-N 4-amino-2,6-dibromobenzoic acid Chemical compound NC1=CC(Br)=C(C(O)=O)C(Br)=C1 WRKHXTXBQDPSEH-UHFFFAOYSA-N 0.000 description 1
- OMVFXCQLSCPJNR-UHFFFAOYSA-N 4-amino-2,6-dimethylphenol Chemical compound CC1=CC(N)=CC(C)=C1O OMVFXCQLSCPJNR-UHFFFAOYSA-N 0.000 description 1
- XPHCXUQZUCONRA-UHFFFAOYSA-N 4-amino-2-butylphenol Chemical compound CCCCC1=CC(N)=CC=C1O XPHCXUQZUCONRA-UHFFFAOYSA-N 0.000 description 1
- QDUSBPJVNWUNJH-UHFFFAOYSA-N 4-amino-2-cyclohexylphenol Chemical compound NC1=CC=C(O)C(C2CCCCC2)=C1 QDUSBPJVNWUNJH-UHFFFAOYSA-N 0.000 description 1
- OUIITAOCYATDMY-UHFFFAOYSA-N 4-amino-2-phenylphenol Chemical compound NC1=CC=C(O)C(C=2C=CC=CC=2)=C1 OUIITAOCYATDMY-UHFFFAOYSA-N 0.000 description 1
- UJGIEAXELCZTOF-UHFFFAOYSA-N 4-amino-3,5-dibromophenol Chemical compound NC1=C(Br)C=C(O)C=C1Br UJGIEAXELCZTOF-UHFFFAOYSA-N 0.000 description 1
- NZEOOPXCKUWJDQ-UHFFFAOYSA-N 4-amino-3,5-dimethylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC(C)=C1N NZEOOPXCKUWJDQ-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- AIXJFGXCCUGURO-UHFFFAOYSA-N 4-amino-3-butylbenzoic acid Chemical compound CCCCC1=CC(C(O)=O)=CC=C1N AIXJFGXCCUGURO-UHFFFAOYSA-N 0.000 description 1
- SAVGBRNEDFZZOZ-UHFFFAOYSA-N 4-amino-3-cyclohexylbenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1C1CCCCC1 SAVGBRNEDFZZOZ-UHFFFAOYSA-N 0.000 description 1
- SXJQUUPSLJTKKT-UHFFFAOYSA-N 4-amino-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1N SXJQUUPSLJTKKT-UHFFFAOYSA-N 0.000 description 1
- CYFVSUQXQFSOAE-UHFFFAOYSA-N 4-amino-3-phenylbenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1C1=CC=CC=C1 CYFVSUQXQFSOAE-UHFFFAOYSA-N 0.000 description 1
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- ROFNJLCLYMMXCT-UHFFFAOYSA-N 4-aminohexanoic acid Chemical compound CCC(N)CCC(O)=O ROFNJLCLYMMXCT-UHFFFAOYSA-N 0.000 description 1
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical compound NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 1
- DRNGLYHKYPNTEA-UHFFFAOYSA-N 4-azaniumylcyclohexane-1-carboxylate Chemical compound NC1CCC(C(O)=O)CC1 DRNGLYHKYPNTEA-UHFFFAOYSA-N 0.000 description 1
- WDTRNCFZFQIWLM-UHFFFAOYSA-N 4-benzylaniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1 WDTRNCFZFQIWLM-UHFFFAOYSA-N 0.000 description 1
- STYQHICBPYRHQK-UHFFFAOYSA-N 4-bromobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Br)C=C1 STYQHICBPYRHQK-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
- HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 description 1
- QCIWHVKGVVQHIY-UHFFFAOYSA-N 4-cyclohexylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1CCCCC1 QCIWHVKGVVQHIY-UHFFFAOYSA-N 0.000 description 1
- WCTPJCYSFNTVKJ-UHFFFAOYSA-N 4-hydroxy-n-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=C(O)C=C1 WCTPJCYSFNTVKJ-UHFFFAOYSA-N 0.000 description 1
- JIICYHFLIOGGHE-UHFFFAOYSA-N 4-methoxybenzene-1,3-dicarboxylic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C(O)=O JIICYHFLIOGGHE-UHFFFAOYSA-N 0.000 description 1
- MSFQEZBRFPAFEX-UHFFFAOYSA-N 4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1 MSFQEZBRFPAFEX-UHFFFAOYSA-N 0.000 description 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 1
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 description 1
- GUXMEUQEXYFYRQ-UHFFFAOYSA-N 4-phenylphenol;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.C1=CC(O)=CC=C1C1=CC=CC=C1.C1=CC(O)=CC=C1C1=CC=CC=C1 GUXMEUQEXYFYRQ-UHFFFAOYSA-N 0.000 description 1
- TZQVSGOOKNNDFU-UHFFFAOYSA-N 4-phenylsulfanylaniline Chemical compound C1=CC(N)=CC=C1SC1=CC=CC=C1 TZQVSGOOKNNDFU-UHFFFAOYSA-N 0.000 description 1
- ALHZRKDYFVXHIJ-UHFFFAOYSA-N 5,5-diphenylcyclooctane-1,1-diol Chemical compound OC1(CCCC(CCC1)(C1=CC=CC=C1)C1=CC=CC=C1)O ALHZRKDYFVXHIJ-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical class CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- DVAJJBDKXKPUKP-UHFFFAOYSA-N 7,7-diphenylcyclododecane-1,1-diol Chemical compound OC1(CCCCCC(CCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1)O DVAJJBDKXKPUKP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FYQRXUOBNXPLRN-HDJSIYSDSA-N C1=CC(C(=O)O)=CC=C1[C@@H]1CC[C@@H](C=2C=CC(=CC=2)C(O)=O)CC1 Chemical compound C1=CC(C(=O)O)=CC=C1[C@@H]1CC[C@@H](C=2C=CC(=CC=2)C(O)=O)CC1 FYQRXUOBNXPLRN-HDJSIYSDSA-N 0.000 description 1
- DJCVCYUEICJZBD-HDJSIYSDSA-N C1=CC(N)=CC=C1[C@@H]1CC[C@@H](C=2C=CC(N)=CC=2)CC1 Chemical compound C1=CC(N)=CC=C1[C@@H]1CC[C@@H](C=2C=CC(N)=CC=2)CC1 DJCVCYUEICJZBD-HDJSIYSDSA-N 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- 0 CC(C)(NC)[Cn]N Chemical compound CC(C)(NC)[Cn]N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 229920001890 Novodur Polymers 0.000 description 1
- KGTYCFGSIMQTAH-UHFFFAOYSA-N OC1(C(CCCCCC(CCCC1)(C1=CC=CC=C1)C1=CC=CC=C1)(OC)OC)O Chemical compound OC1(C(CCCCCC(CCCC1)(C1=CC=CC=C1)C1=CC=CC=C1)(OC)OC)O KGTYCFGSIMQTAH-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- RPYFJVIASOJLJS-UHFFFAOYSA-N [3-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine Chemical compound C1CC2C(CN)C(CN)C1C2 RPYFJVIASOJLJS-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 229960000250 adipic acid Drugs 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- ZWOASCVFHSYHOB-UHFFFAOYSA-N benzene-1,3-dithiol Chemical compound SC1=CC=CC(S)=C1 ZWOASCVFHSYHOB-UHFFFAOYSA-N 0.000 description 1
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000005130 benzoxazines 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
- VUFQYRAKSQTZEB-UHFFFAOYSA-N bicyclo[2.2.1]heptan-4-amine Chemical compound C1CC2CCC1(N)C2 VUFQYRAKSQTZEB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- PZKYPEIOGNUSOC-UHFFFAOYSA-N bis(4-hydroxyphenyl) benzene-1,4-dicarboxylate Chemical compound C1=CC(O)=CC=C1OC(=O)C1=CC=C(C(=O)OC=2C=CC(O)=CC=2)C=C1 PZKYPEIOGNUSOC-UHFFFAOYSA-N 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical group CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- QQKBIYRSRXCROF-UHFFFAOYSA-N cyclohexane-1,4-dithiol Chemical compound SC1CCC(S)CC1 QQKBIYRSRXCROF-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- SUNVJLYYDZCIIK-UHFFFAOYSA-N durohydroquinone Chemical compound CC1=C(C)C(O)=C(C)C(C)=C1O SUNVJLYYDZCIIK-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- HZZUMXSLPJFMCB-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;acetate Chemical compound CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 HZZUMXSLPJFMCB-UHFFFAOYSA-M 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000009787 hand lay-up Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000004704 methoxides Chemical class 0.000 description 1
- RLIWLEROXZTIIT-UHFFFAOYSA-M methyl-tris(2-methylphenyl)phosphanium;chloride Chemical compound [Cl-].CC1=CC=CC=C1[P+](C)(C=1C(=CC=CC=1)C)C1=CC=CC=C1C RLIWLEROXZTIIT-UHFFFAOYSA-M 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical compound [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000015149 toffees Nutrition 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- PPQRADLPLZYEKN-UHFFFAOYSA-N tritylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 PPQRADLPLZYEKN-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting 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
- C08G59/182—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
-
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26579909P | 2009-12-02 | 2009-12-02 | |
| US61/265,799 | 2009-12-02 | ||
| PCT/US2010/056102 WO2011068644A1 (en) | 2009-12-02 | 2010-11-10 | Epoxy resin compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013512988A true JP2013512988A (ja) | 2013-04-18 |
| JP2013512988A5 JP2013512988A5 (enExample) | 2013-12-12 |
Family
ID=43769749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012542034A Pending JP2013512988A (ja) | 2009-12-02 | 2010-11-10 | エポキシ樹脂組成物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8937145B2 (enExample) |
| EP (1) | EP2507283B1 (enExample) |
| JP (1) | JP2013512988A (enExample) |
| KR (1) | KR20120101096A (enExample) |
| CN (1) | CN102648227B (enExample) |
| SG (1) | SG181461A1 (enExample) |
| TW (1) | TWI488879B (enExample) |
| WO (1) | WO2011068644A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013512989A (ja) * | 2009-12-02 | 2013-04-18 | ダウ グローバル テクノロジーズ エルエルシー | コーティング組成物 |
| 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 |
| JP2018109197A (ja) * | 2015-02-17 | 2018-07-12 | 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 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG181461A1 (en) | 2009-12-02 | 2012-07-30 | Dow Global Technologies Llc | Epoxy resin compositions |
| US9006312B2 (en) * | 2009-12-02 | 2015-04-14 | Dow Global Technologies Llc | Composite compositions |
| JP5752784B2 (ja) | 2010-04-16 | 2015-07-22 | ヴァルスパー・ソーシング・インコーポレーテッド | パッケージ物品用のコーティング組成物及びコーティング方法 |
| US8519066B2 (en) | 2010-04-29 | 2013-08-27 | Dow Global Technologies Llc | Poly(allyl ethers) of polycyclopentadiene polyphenol |
| SG184834A1 (en) | 2010-04-29 | 2012-11-29 | Dow Global Technologies Llc | Polycyclopentadiene polyphenol and polycyanate polycyclopentadiene polyphenol compounds |
| EP2563755A1 (en) | 2010-04-29 | 2013-03-06 | Dow Global Technologies LLC | Vinylbenzyl ethers of polycyclopentadiene polyphenol |
| WO2012109278A2 (en) | 2011-02-07 | 2012-08-16 | Valspar Sourcing, Inc. | Coating compositions for containers and other articles and methods of coating |
| EP2702029B1 (en) | 2011-04-27 | 2017-06-07 | University Of Massachusetts Lowell | Bisphenol a (bpa) free epoxy resins |
| US9309381B2 (en) | 2011-06-24 | 2016-04-12 | Air Products And Chemicals, Inc. | Epoxy resin compositions using solvated solids |
| US20120328811A1 (en) * | 2011-06-24 | 2012-12-27 | Air Products And Chemicals, Inc. | Epoxy Resin Compositions |
| CN104159941A (zh) | 2012-02-24 | 2014-11-19 | 陶氏环球技术有限责任公司 | 环十二烷多酚的多氰酸酯及其热固性材料 |
| BR112014018939B1 (pt) * | 2012-02-24 | 2021-02-23 | Dow Global Technologies Llc | Poliglicidil éteres, métodos para preparar os compostos, composiçõescuradas e adutos |
| 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 |
| IN2015DN00445A (enExample) | 2012-08-09 | 2015-06-19 | Valspar Sourcing Inc | |
| 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 |
| WO2015103427A1 (en) | 2013-12-31 | 2015-07-09 | Saint-Gobain Performance Plastics Corporation | Composites for protecting signal transmitters/receivers |
| JP6746501B2 (ja) | 2014-04-14 | 2020-08-26 | ヴァルスパー・ソーシング・インコーポレーテッド | 容器及び他の物品のための組成物の調製方法並びにその使用方法 |
| 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 |
| CA3032191C (en) * | 2016-07-25 | 2023-08-29 | Isola Usa Corp. | Improved styrene maleic anhydride (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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0892351A (ja) * | 1994-09-26 | 1996-04-09 | Nippon Kayaku Co Ltd | エポキシ樹脂、エポキシ樹脂組成物およびその硬化物 |
| JP2006251496A (ja) * | 2005-03-11 | 2006-09-21 | Toppan Printing Co Ltd | アルカリ現像型感光性着色組成物、及びそれを用いたカラーフィルタ |
| JP2006259249A (ja) * | 2005-03-17 | 2006-09-28 | Shin Etsu Chem Co Ltd | フォトレジスト下層膜形成材料及びパターン形成方法 |
| JP2007254579A (ja) * | 2006-03-23 | 2007-10-04 | Nippon Kayaku Co Ltd | エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
| JP2011001447A (ja) * | 2009-06-18 | 2011-01-06 | Nippon Kayaku Co Ltd | エポキシ樹脂組成物 |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018262A (en) | 1957-05-01 | 1962-01-23 | Shell Oil Co | Curing polyepoxides with certain metal salts of inorganic acids |
| DE1495841A1 (de) | 1964-10-27 | 1969-04-10 | Bayer Ag | Verfahren zur Herstellung hochmolekularer Polycarbonate |
| CH571511A5 (enExample) | 1972-04-21 | 1976-01-15 | Ciba Geigy Ag | |
| US4638027A (en) | 1982-12-27 | 1987-01-20 | General Electric Company | Polycarbonate exhibiting improved heat resistance from cycloalkylidene diphenol |
| US4438241A (en) * | 1982-12-27 | 1984-03-20 | General Electric Company | Heat resistant polyarylates |
| US4707534A (en) | 1986-12-09 | 1987-11-17 | Minnesota Mining And Manufacturing Company | Glycidylethers of fluorene-containing bisphenols |
| US4925901A (en) | 1988-02-12 | 1990-05-15 | The Dow Chemical Company | Latent, curable, catalyzed mixtures of epoxy-containing and phenolic hydroxyl-containing compounds |
| NO170326C (no) | 1988-08-12 | 1992-10-07 | Bayer Ag | Dihydroksydifenylcykloalkaner |
| CN1029122C (zh) * | 1988-08-12 | 1995-06-28 | 拜尔公司 | 二羟基二苯基环烷烃，其制备方法及其在制备高分子量聚碳酸酯中的应用 |
| US5463091A (en) | 1989-01-17 | 1995-10-31 | The Dow Chemical Company | Diglycidyl ether of 4,4'-dihydroxy-α-methylstilbene |
| DE58907953D1 (de) | 1989-03-03 | 1994-07-28 | Siemens Ag | Epoxidharzmischungen. |
| US5135993A (en) | 1990-09-11 | 1992-08-04 | Dow Corning Corporation | High modulus silicones as toughening agents for epoxy resins |
| US5369192A (en) | 1993-06-28 | 1994-11-29 | Minnesota Mining And Manufacturing Company | Binder resin for resin transfer molding preforms |
| US5401814A (en) | 1993-10-13 | 1995-03-28 | The Dow Chemical Company | Process for the preparation of thermoplastic poly(hydroxy ethers) |
| GB9411367D0 (en) | 1994-06-07 | 1994-07-27 | Ici Composites Inc | Curable Composites |
| DE19539444A1 (de) | 1995-10-24 | 1997-04-30 | Bayer Ag | Verfahren zur Herstellung von Bisphenolen unter Verwendung neuer Cokatalysatoren |
| CN1171219A (zh) | 1996-07-24 | 1998-01-28 | 藤泽光男 | 具有装饰花纹的片料 |
| US6613839B1 (en) * | 1997-01-21 | 2003-09-02 | The Dow Chemical Company | Polyepoxide, catalyst/cure inhibitor complex and anhydride |
| JP3734602B2 (ja) | 1997-05-29 | 2006-01-11 | ジャパンエポキシレジン株式会社 | エポキシ樹脂組成物および半導体封止用エポキシ樹脂組成物 |
| GB9713526D0 (en) | 1997-06-26 | 1997-09-03 | Dow Deutschland Inc | Flame retardant laminating formulations |
| US6153719A (en) | 1998-02-04 | 2000-11-28 | Lord Corporation | Thiol-cured epoxy composition |
| US6632893B2 (en) | 1999-05-28 | 2003-10-14 | Henkel Loctite Corporation | Composition of epoxy resin, cyanate ester, imidazole and polysulfide tougheners |
| US6576718B1 (en) | 1999-10-05 | 2003-06-10 | General Electric Company | Powder coating of thermosetting resin(s) and poly(phenylene ethers(s)) |
| WO2001042253A2 (en) | 1999-12-13 | 2001-06-14 | The Dow Chemical Company | Phosphorus element-containing crosslinking agents and flame retardant phosphorus element-containing epoxy resin compositions prepared therewith |
| KR100721697B1 (ko) | 1999-12-13 | 2007-05-28 | 다우 글로벌 테크놀로지스 인크. | 난연성 인 원소 함유 에폭시 수지 조성물 |
| 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 |
| DE10208743A1 (de) | 2002-02-28 | 2003-12-11 | Siemens Ag | Korrosionsarme Epoxidharze und Herstellungsverfahren dazu |
| 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 |
| JP4698586B2 (ja) | 2004-03-25 | 2011-06-08 | 株式会社Ａｄｅｋａ | 新規フェノール化合物及び該フェノール化合物から誘導し得る新規エポキシ樹脂 |
| WO2005118604A1 (en) | 2004-05-28 | 2005-12-15 | Dow Global Technologies Inc. | Phosphorus-containing compounds useful for making halogen-free, ignition-resistant polymers |
| MX2007005597A (es) | 2004-11-10 | 2007-05-23 | Dow Global Technologies Inc | Resinas epoxicas endurecidas con copolimero de bloque anfifilico y laminados electricos hechos de las mismas. |
| US8048819B2 (en) | 2005-06-23 | 2011-11-01 | Momentive Performance Materials Inc. | Cure catalyst, composition, electronic device and associated method |
| JP2010540754A (ja) | 2007-10-05 | 2010-12-24 | ダウ グローバル テクノロジーズ インコーポレイティド | イソシアネート変性エポキシ樹脂及びそのエポキシ粉体コーティング組成物 |
| CN101842401B (zh) | 2007-10-31 | 2015-06-24 | 陶氏环球技术公司 | 用于熔融粘结环氧树脂应用的非烧结异氰酸酯改性环氧树脂 |
| DE602007008593D1 (de) | 2007-12-12 | 2010-09-30 | Atotech Deutschland Gmbh | Festpulverformulierungen für die Zubereitung von harzbeschichteten Folien und ihre Verwendung bei der Herstellung von Leiterplatten |
| DE102008008841A1 (de) | 2008-02-13 | 2009-08-20 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polycarbonaten |
| JP5722636B2 (ja) | 2008-03-12 | 2015-05-27 | ダウ グローバル テクノロジーズ エルエルシー | 脂肪族炭素含有量が大きい芳香族ジシアナート化合物 |
| JP5871326B2 (ja) * | 2009-12-02 | 2016-03-01 | ブルー キューブ アイピー エルエルシー | コーティング組成物 |
| US9006312B2 (en) * | 2009-12-02 | 2015-04-14 | Dow Global Technologies Llc | Composite compositions |
| SG181461A1 (en) | 2009-12-02 | 2012-07-30 | Dow Global Technologies Llc | Epoxy resin compositions |
-
2010
- 2010-11-10 SG SG2012040291A patent/SG181461A1/en unknown
- 2010-11-10 WO PCT/US2010/056102 patent/WO2011068644A1/en not_active Ceased
- 2010-11-10 KR KR1020127016913A patent/KR20120101096A/ko not_active Ceased
- 2010-11-10 EP EP10778810.1A patent/EP2507283B1/en not_active Not-in-force
- 2010-11-10 CN CN201080054831.7A patent/CN102648227B/zh active Active
- 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
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0892351A (ja) * | 1994-09-26 | 1996-04-09 | Nippon Kayaku Co Ltd | エポキシ樹脂、エポキシ樹脂組成物およびその硬化物 |
| JP2006251496A (ja) * | 2005-03-11 | 2006-09-21 | Toppan Printing Co Ltd | アルカリ現像型感光性着色組成物、及びそれを用いたカラーフィルタ |
| JP2006259249A (ja) * | 2005-03-17 | 2006-09-28 | Shin Etsu Chem Co Ltd | フォトレジスト下層膜形成材料及びパターン形成方法 |
| JP2007254579A (ja) * | 2006-03-23 | 2007-10-04 | Nippon Kayaku Co Ltd | エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
| JP2011001447A (ja) * | 2009-06-18 | 2011-01-06 | Nippon Kayaku Co Ltd | エポキシ樹脂組成物 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013512989A (ja) * | 2009-12-02 | 2013-04-18 | ダウ グローバル テクノロジーズ エルエルシー | コーティング組成物 |
| 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 |
| JP2018109197A (ja) * | 2015-02-17 | 2018-07-12 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI488879B (zh) | 2015-06-21 |
| US20120238709A1 (en) | 2012-09-20 |
| SG181461A1 (en) | 2012-07-30 |
| CN102648227B (zh) | 2015-08-26 |
| TW201136971A (en) | 2011-11-01 |
| US8937145B2 (en) | 2015-01-20 |
| EP2507283A1 (en) | 2012-10-10 |
| CN102648227A (zh) | 2012-08-22 |
| EP2507283B1 (en) | 2013-10-23 |
| WO2011068644A1 (en) | 2011-06-09 |
| KR20120101096A (ko) | 2012-09-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI488879B (zh) | 環氧樹脂組成物 | |
| US9006312B2 (en) | Composite compositions | |
| JP5871326B2 (ja) | コーティング組成物 | |
| DK2621992T3 (en) | Epoxy resin adducts and thermoplastic materials thereof | |
| JP5719562B2 (ja) | 高分子量エポキシ樹脂、該高分子量エポキシ樹脂を用いる樹脂フィルム、樹脂組成物、および硬化物 | |
| CN101910238A (zh) | 用于复合材料应用的高Tg环氧体系 | |
| JP2011521073A (ja) | エポキシ樹脂のアダクト及びその製造方法 | |
| US20120245306A1 (en) | Adducts based on divinylarene oxides | |
| HK1170516A (en) | Epoxy resin compositions | |
| JP2024075955A (ja) | 炭素繊維強化プラスチック用エポキシ樹脂組成物及び硬化物 | |
| HK1170521A (en) | Coating compositions | |
| HK1170754A (en) | Composite compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131022 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20131022 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140318 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140319 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140612 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20141118 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150204 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150721 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20151020 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151116 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20151221 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20160419 |