CA3031544C - Resine epoxy - Google Patents
Resine epoxy Download PDFInfo
- Publication number
- CA3031544C CA3031544C CA3031544A CA3031544A CA3031544C CA 3031544 C CA3031544 C CA 3031544C CA 3031544 A CA3031544 A CA 3031544A CA 3031544 A CA3031544 A CA 3031544A CA 3031544 C CA3031544 C CA 3031544C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- epoxy resin
- curable epoxy
- resin formulation
- 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.)
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 157
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 154
- 150000001875 compounds Chemical class 0.000 claims abstract description 193
- 239000000203 mixture Substances 0.000 claims abstract description 132
- 238000009472 formulation Methods 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000002131 composite material Substances 0.000 claims abstract description 25
- 239000000835 fiber Substances 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 63
- 239000000463 material Substances 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 150000004985 diamines Chemical group 0.000 claims description 18
- 239000004593 Epoxy Substances 0.000 claims description 17
- 239000002657 fibrous material Substances 0.000 claims description 16
- 239000011159 matrix material Substances 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 239000004760 aramid Substances 0.000 claims description 5
- 229920003235 aromatic polyamide Polymers 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000011417 postcuring Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 239000011152 fibreglass Substances 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 abstract description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 13
- -1 compounds epoxide Chemical class 0.000 abstract description 11
- 238000010348 incorporation Methods 0.000 abstract description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 94
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 238000003786 synthesis reaction Methods 0.000 description 52
- 230000015572 biosynthetic process Effects 0.000 description 51
- 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 50
- 239000000047 product Substances 0.000 description 49
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 47
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 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 35
- 239000000243 solution Substances 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 27
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 235000011121 sodium hydroxide Nutrition 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- 229960004592 isopropanol Drugs 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000000523 sample Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000007832 Na2SO4 Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 239000012265 solid product Substances 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- TYOMCHWDDNQYHU-UHFFFAOYSA-N 2-[[3-[3-[3-(oxiran-2-ylmethoxy)phenoxy]phenoxy]phenoxy]methyl]oxirane Chemical compound C(C1CO1)OC=1C=C(OC2=CC(=CC=C2)OC2=CC(=CC=C2)OCC2CO2)C=CC=1 TYOMCHWDDNQYHU-UHFFFAOYSA-N 0.000 description 7
- HURSUNYVRTZMIX-UHFFFAOYSA-N 2-[[4-[4-[4-(oxiran-2-ylmethoxy)phenoxy]phenoxy]phenoxy]methyl]oxirane Chemical compound C(C1CO1)OC1=CC=C(OC2=CC=C(C=C2)OC2=CC=C(C=C2)OCC2CO2)C=C1 HURSUNYVRTZMIX-UHFFFAOYSA-N 0.000 description 7
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 239000004848 polyfunctional curative Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HIXFSHWMTVMNID-UHFFFAOYSA-N 1,3-bis(3-methoxyphenoxy)benzene Chemical compound COC1=CC=CC(OC=2C=C(OC=3C=C(OC)C=CC=3)C=CC=2)=C1 HIXFSHWMTVMNID-UHFFFAOYSA-N 0.000 description 4
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 4
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- RLSMYIFSFZLJQZ-UHFFFAOYSA-N 4-[4-(4-hydroxyphenoxy)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(O)C=C1 RLSMYIFSFZLJQZ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- UVXIFYUJZWURAR-UHFFFAOYSA-N [3-(4-aminobenzoyl)phenyl]-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 UVXIFYUJZWURAR-UHFFFAOYSA-N 0.000 description 3
- DBCMPVCYHLRHND-UHFFFAOYSA-N [4-(4-aminobenzoyl)phenyl]-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(C(=O)C=2C=CC(N)=CC=2)C=C1 DBCMPVCYHLRHND-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- GJKFIJKSBFYMQK-UHFFFAOYSA-N lanthanum(3+);trinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GJKFIJKSBFYMQK-UHFFFAOYSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 210000003739 neck Anatomy 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000013341 scale-up Methods 0.000 description 3
- 238000002076 thermal analysis method Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-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
- OZBAMTFRHADAKN-UHFFFAOYSA-N 2-[2-(2-hydroxyphenyl)-3,6-dimethylphenyl]phenol Chemical group OC1=C(C=CC=C1)C=1C(=C(C=CC=1C)C)C1=C(C=CC=C1)O OZBAMTFRHADAKN-UHFFFAOYSA-N 0.000 description 2
- XJJYJJKMQRFGQM-UHFFFAOYSA-N 3-[3-(3-hydroxyphenoxy)phenoxy]phenol Chemical compound OC1=CC=CC(OC=2C=C(OC=3C=C(O)C=CC=3)C=CC=2)=C1 XJJYJJKMQRFGQM-UHFFFAOYSA-N 0.000 description 2
- MERLDGDYUMSLAY-UHFFFAOYSA-N 4-[(4-aminophenyl)disulfanyl]aniline Chemical compound C1=CC(N)=CC=C1SSC1=CC=C(N)C=C1 MERLDGDYUMSLAY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- GUWUXDXPVSIMQF-UHFFFAOYSA-N CC1=CC(C)=C(C=2C=CC(O)=CC=2)C=C1C1=CC=C(O)C=C1 Chemical group CC1=CC(C)=C(C=2C=CC(O)=CC=2)C=C1C1=CC=C(O)C=C1 GUWUXDXPVSIMQF-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 238000012565 NMR experiment Methods 0.000 description 2
- CTQZSSWIJYMLOG-UHFFFAOYSA-N OC1=CC(=C(C(=C1C)C1=CC=CC=C1)C)O Chemical group OC1=CC(=C(C(=C1C)C1=CC=CC=C1)C)O CTQZSSWIJYMLOG-UHFFFAOYSA-N 0.000 description 2
- AYLRNSZYYYKPCJ-UHFFFAOYSA-N OC=1C(=C(C(=C(C=1)C)C1=CC=CC=C1)O)C Chemical group OC=1C(=C(C(=C(C=1)C)C1=CC=CC=C1)O)C AYLRNSZYYYKPCJ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- IVGBGCPUDUTSHT-UHFFFAOYSA-N [3-(3-aminobenzoyl)phenyl]-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(C=CC=2)C(=O)C=2C=C(N)C=CC=2)=C1 IVGBGCPUDUTSHT-UHFFFAOYSA-N 0.000 description 2
- NDROPZAZVXXQSC-UHFFFAOYSA-N [4-[4-(4-acetyloxyphenoxy)phenoxy]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(OC(C)=O)C=C1 NDROPZAZVXXQSC-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 230000016507 interphase Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- SFPXVPWDXSCTBK-UHFFFAOYSA-N 1,5-dichloro-2,4-dimethylbenzene Chemical group CC1=CC(C)=C(Cl)C=C1Cl SFPXVPWDXSCTBK-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- UGHIQYNKFXEQPU-UHFFFAOYSA-N 2,3-dichloro-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Cl)=C1Cl UGHIQYNKFXEQPU-UHFFFAOYSA-N 0.000 description 1
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
- FIHIZQGYHRJNJU-UHFFFAOYSA-N 2-[[4-[3-[4-(oxiran-2-ylmethoxy)phenoxy]phenoxy]phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OC(C=1)=CC=CC=1OC(C=C1)=CC=C1OCC1CO1 FIHIZQGYHRJNJU-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
- C08L2205/16—Fibres; Fibrils
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Resins (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA3231558A CA3231558A1 (fr) | 2016-07-25 | 2017-07-20 | Resine epoxy |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662366443P | 2016-07-25 | 2016-07-25 | |
US62/366,443 | 2016-07-25 | ||
AU2016904019 | 2016-10-04 | ||
AU2016904019A AU2016904019A0 (en) | 2016-10-04 | Epoxy resin | |
PCT/AU2017/050748 WO2018018070A1 (fr) | 2016-07-25 | 2017-07-20 | Résine époxy |
Related Child Applications (1)
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CA3231558A Division CA3231558A1 (fr) | 2016-07-25 | 2017-07-20 | Resine epoxy |
Publications (2)
Publication Number | Publication Date |
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CA3031544A1 CA3031544A1 (fr) | 2018-02-01 |
CA3031544C true CA3031544C (fr) | 2024-04-23 |
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Application Number | Title | Priority Date | Filing Date |
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CA3031544A Active CA3031544C (fr) | 2016-07-25 | 2017-07-20 | Resine epoxy |
Country Status (3)
Country | Link |
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AU (1) | AU2017301100B2 (fr) |
CA (1) | CA3031544C (fr) |
WO (1) | WO2018018070A1 (fr) |
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CN109796312A (zh) * | 2019-02-12 | 2019-05-24 | 上海阿拉丁生化科技股份有限公司 | 一种3-羟基联苯的合成方法 |
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US3219670A (en) * | 1961-09-29 | 1965-11-23 | Minnesota Mining & Mfg | Glycidyl ethers of poly(hydroxyphenoxy) aromatic compounds |
EP0157740B1 (fr) | 1984-04-04 | 1990-06-27 | Ciba-Geigy Ag | Glycidyloxydicétones |
JPS62114981A (ja) * | 1985-11-15 | 1987-05-26 | Toray Ind Inc | 新規エポキシ樹脂 |
SE530059C2 (sv) * | 2006-03-06 | 2008-02-19 | Perstorp Specialty Chem Ab | Förfarande för framställning av en bis-ftalonitrilmonomer |
KR101524485B1 (ko) * | 2008-03-03 | 2015-06-01 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | 변성 에폭시수지, 에폭시수지 조성물 및 경화물 |
US9309353B2 (en) * | 2013-08-09 | 2016-04-12 | The Boeing Company | Formulation methodology for distortional thermosets |
CN104761874B (zh) | 2015-04-14 | 2017-04-05 | 东华大学 | 一种耐高温碳纤维增强电缆芯用拉挤树脂及其制备方法 |
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2017
- 2017-07-20 WO PCT/AU2017/050748 patent/WO2018018070A1/fr active Search and Examination
- 2017-07-20 CA CA3031544A patent/CA3031544C/fr active Active
- 2017-07-20 AU AU2017301100A patent/AU2017301100B2/en active Active
Also Published As
Publication number | Publication date |
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WO2018018070A1 (fr) | 2018-02-01 |
AU2017301100A1 (en) | 2019-02-14 |
CA3031544A1 (fr) | 2018-02-01 |
AU2017301100B2 (en) | 2021-08-12 |
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