TW201002751A - Adducts of epoxy resins and process for preparing the same - Google Patents
Adducts of epoxy resins and process for preparing the same Download PDFInfo
- Publication number
- TW201002751A TW201002751A TW098116880A TW98116880A TW201002751A TW 201002751 A TW201002751 A TW 201002751A TW 098116880 A TW098116880 A TW 098116880A TW 98116880 A TW98116880 A TW 98116880A TW 201002751 A TW201002751 A TW 201002751A
- Authority
- TW
- Taiwan
- Prior art keywords
- epoxy resin
- adduct
- trans
- cis
- resin material
- Prior art date
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 187
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 186
- 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 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 143
- 239000000463 material Substances 0.000 claims abstract description 91
- 239000000203 mixture Substances 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 60
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 54
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 41
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 20
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 105
- 238000006243 chemical reaction Methods 0.000 claims description 85
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 77
- 239000000047 product Substances 0.000 claims description 77
- 229920005989 resin Polymers 0.000 claims description 63
- 239000011347 resin Substances 0.000 claims description 63
- -1 dimethyl diglycidyl ether Chemical compound 0.000 claims description 60
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 28
- 238000005266 casting Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 15
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 11
- LUSFFPXRDZKBMF-OCAPTIKFSA-N [(1s,3r)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@@H](CO)C1 LUSFFPXRDZKBMF-OCAPTIKFSA-N 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229920000768 polyamine Polymers 0.000 claims description 6
- 235000013824 polyphenols Nutrition 0.000 claims description 6
- 230000009257 reactivity Effects 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- LUSFFPXRDZKBMF-YUMQZZPRSA-N [(1s,3s)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@H](CO)C1 LUSFFPXRDZKBMF-YUMQZZPRSA-N 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QTAFORZADPHKBK-UHFFFAOYSA-N 1,2-bis(oxiran-2-ylmethyl)hydrazine Chemical compound C(C1CO1)NNCC1CO1 QTAFORZADPHKBK-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- OLLMEZGFCPWTGD-UHFFFAOYSA-N hexane;methanol Chemical compound OC.OC.CCCCCC OLLMEZGFCPWTGD-UHFFFAOYSA-N 0.000 claims description 3
- 229910000069 nitrogen hydride Inorganic materials 0.000 claims description 3
- 229920006295 polythiol Polymers 0.000 claims description 3
- VQMQXWYQIIUJIT-HXZBBRIXSA-N C(OC[C@H]1CC[C@H](COCC2CO2)CC1)C1CO1 Chemical compound C(OC[C@H]1CC[C@H](COCC2CO2)CC1)C1CO1 VQMQXWYQIIUJIT-HXZBBRIXSA-N 0.000 claims description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000009730 filament winding Methods 0.000 claims description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims 3
- 239000004970 Chain extender Substances 0.000 claims 1
- IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 claims 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 150000008442 polyphenolic compounds Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 11
- 230000009274 differential gene expression Effects 0.000 description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 150000001412 amines Chemical class 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- 238000007792 addition Methods 0.000 description 25
- 150000002118 epoxides Chemical class 0.000 description 25
- 238000004448 titration Methods 0.000 description 24
- 239000001257 hydrogen Substances 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
- 238000004817 gas chromatography Methods 0.000 description 19
- 239000007788 liquid Substances 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 19
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 239000011521 glass Substances 0.000 description 16
- 239000000376 reactant Substances 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 15
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 14
- 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 13
- 238000000113 differential scanning calorimetry Methods 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 11
- 238000012512 characterization method Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000006735 epoxidation reaction Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- 229960001428 mercaptopurine Drugs 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920001187 thermosetting polymer Polymers 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 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-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
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000012937 correction Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- 229920003023 plastic Polymers 0.000 description 4
- 238000011417 postcuring Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
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- 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
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
- 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 3
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 3
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 3
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- 239000001307 helium Substances 0.000 description 3
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- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 3
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- CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 2
- LNOLJFCCYQZFBQ-BUHFOSPRSA-N (ne)-n-[(4-nitrophenyl)-phenylmethylidene]hydroxylamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=N/O)/C1=CC=CC=C1 LNOLJFCCYQZFBQ-BUHFOSPRSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-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
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- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
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- NINOYJQVULROET-UHFFFAOYSA-N n,n-dimethylethenamine Chemical compound CN(C)C=C NINOYJQVULROET-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LIXVMPBOGDCSRM-UHFFFAOYSA-N nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1 LIXVMPBOGDCSRM-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- RCYPXVCYMDSECE-UHFFFAOYSA-N oxiran-2-ylmethylhydrazine Chemical compound NNCC1CO1 RCYPXVCYMDSECE-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- JJAIIULJXXEFLV-UHFFFAOYSA-N pentane-2,3,4-triol Chemical compound CC(O)C(O)C(C)O JJAIIULJXXEFLV-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- DBIWHDFLQHGOCS-UHFFFAOYSA-N piperidine;trifluoroborane Chemical compound FB(F)F.C1CCNCC1 DBIWHDFLQHGOCS-UHFFFAOYSA-N 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- NKCRONNLHOVFPV-UHFFFAOYSA-N purin-4-amine Chemical compound C1=NC=NC2(N)C1=NC=N2 NKCRONNLHOVFPV-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- UTEALUXXARGFST-UHFFFAOYSA-N ruthenium 1,3,5-triazine-2,4,6-triamine Chemical class N1=C(N)N=C(N)N=C1N.[Ru] UTEALUXXARGFST-UHFFFAOYSA-N 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- ZGYRTJADPPDDMY-UHFFFAOYSA-N titanium;tetrahydrate Chemical compound O.O.O.O.[Ti] ZGYRTJADPPDDMY-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 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
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5523208P | 2008-05-22 | 2008-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201002751A true TW201002751A (en) | 2010-01-16 |
Family
ID=40848204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098116880A TW201002751A (en) | 2008-05-22 | 2009-05-21 | Adducts of epoxy resins and process for preparing the same |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110040046A1 (https=) |
| EP (1) | EP2283060A1 (https=) |
| JP (1) | JP5390599B2 (https=) |
| CN (1) | CN102037049B (https=) |
| TW (1) | TW201002751A (https=) |
| WO (1) | WO2009142898A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI612125B (zh) * | 2013-12-18 | 2018-01-21 | Rohm And Haas Electronic Materials Llc | 可變換之波長轉換介質 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110054056A1 (en) * | 2008-05-22 | 2011-03-03 | Hefner Jr Robert E | Thermoset polyurethanes |
| CN102947261A (zh) | 2010-04-29 | 2013-02-27 | 陶氏环球技术有限责任公司 | 聚环戊二烯多酚的聚(烯丙基醚) |
| EP2563755A1 (en) | 2010-04-29 | 2013-03-06 | Dow Global Technologies LLC | Vinylbenzyl ethers of polycyclopentadiene polyphenol |
| CN105175988A (zh) | 2010-04-29 | 2015-12-23 | 陶氏环球技术有限责任公司 | 聚环戊二烯多酚和聚氰酸酯聚环戊二烯多酚化合物 |
| KR101840073B1 (ko) | 2010-09-30 | 2018-04-26 | 블루 큐브 아이피 엘엘씨 | 에폭시 수지의 제조 방법 |
| US9068039B2 (en) | 2010-09-30 | 2015-06-30 | Dow Global Technologies Llc | Thermosettable compositions and thermosets therefrom |
| CN103154071B (zh) * | 2010-09-30 | 2016-06-15 | 蓝立方知识产权有限责任公司 | 涂料组合物 |
| EP2621994A1 (en) * | 2010-09-30 | 2013-08-07 | Dow Global Technologies LLC | Epoxy resin compositions |
| WO2012050688A2 (en) | 2010-09-30 | 2012-04-19 | Dow Global Technologies Llc | Epoxy resin adducts and thermosets thereof |
| JP2013539804A (ja) * | 2010-09-30 | 2013-10-28 | ダウ グローバル テクノロジーズ エルエルシー | アドバンストエポキシ樹脂組成物 |
| BR112013005067A2 (pt) | 2010-09-30 | 2019-09-24 | Dow Global Technologies Llc | composição de revestimento curável,revestimento curado,processo para preparar um artigo revestido e artigo |
| BR112013033451A2 (pt) * | 2011-07-01 | 2017-01-31 | Dow Global Technologies Llc | aduto de resina epoxi híbrida, processo para preparar um aduto de resina epoxi híbrida, composição de resina epoxi curável, processo para preparar uma composição de resina epoxi curável, produto termofixo de estágio b, processo de estagiamento b de uma resina epoxi, produto termofixo curado, processo para curar uma composição de resina epoxi e artigo |
| WO2013172199A1 (ja) * | 2012-05-16 | 2013-11-21 | 株式会社ダイセル | 硬化性樹脂組成物及びその硬化物、プリプレグ、並びに繊維強化複合材料 |
| JP6130502B2 (ja) * | 2012-07-03 | 2017-05-17 | スリーエム イノベイティブ プロパティズ カンパニー | 構造化ハイブリッド接着剤物品の製造方法 |
| JP2016500744A (ja) | 2012-10-24 | 2016-01-14 | ダウ グローバル テクノロジーズ エルエルシー | 常温硬化耐候性コーティング |
| KR20150079620A (ko) * | 2012-10-24 | 2015-07-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 내후성 코팅 |
| KR20150079611A (ko) | 2012-10-24 | 2015-07-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 부가물 경화제 |
| CN105229095A (zh) * | 2012-12-14 | 2016-01-06 | 蓝立方知识产权有限责任公司 | 高含固量环氧树脂涂料 |
| JP6306419B2 (ja) * | 2014-04-28 | 2018-04-04 | 株式会社クラレ | モノグリシジルエーテル化合物、及びモノアリルエーテル化合物 |
| DE102016203867A1 (de) * | 2016-03-09 | 2017-09-14 | Siemens Aktiengesellschaft | Fester Isolationswerkstoff, Verwendung dazu und damit hergestelltes Isolationssystem |
| CN113045438A (zh) * | 2021-03-11 | 2021-06-29 | 深圳飞扬兴业科技有限公司 | 一种多元伯胺化合物及其制备方法和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297724A (en) * | 1961-03-07 | 1967-01-10 | Eastman Kodak Co | Diepoxides |
| GB1053340A (https=) * | 1963-10-14 | 1900-01-01 | ||
| US4417033A (en) * | 1982-06-01 | 1983-11-22 | Wilmington Chemical Corporation | Diglycidyl ether of dimethanol cyclohexane and reaction products thereof |
| AU571499B2 (en) * | 1983-04-01 | 1988-04-21 | Dow Chemical Company, The | Preparing epoxy resins |
| US4578453A (en) * | 1984-11-23 | 1986-03-25 | Eastman Kodak Company | High molecular weight polyesters |
| US4623701A (en) * | 1985-07-10 | 1986-11-18 | The Dow Chemical Company | Multifunctional epoxy resins |
| US5300541A (en) * | 1988-02-04 | 1994-04-05 | Ppg Industries, Inc. | Polyamine-polyepoxide gas barrier coatings |
| US5463091A (en) * | 1989-01-17 | 1995-10-31 | The Dow Chemical Company | Diglycidyl ether of 4,4'-dihydroxy-α-methylstilbene |
| US5310770A (en) * | 1992-12-30 | 1994-05-10 | Hi-Tek Polymers, Inc. | Water reducible epoxy-amine adducts based on the diglycidyl ether of cyclohexane dimethanol |
| US6218482B1 (en) * | 1994-02-24 | 2001-04-17 | New Japan Chemical Co., Ltd. | Epoxy resin, process for preparing the resin and photo-curable resin composition and resin composition for powder coatings containing the epoxy resin |
| JP3663861B2 (ja) * | 1997-12-03 | 2005-06-22 | 三菱瓦斯化学株式会社 | 新規な樹脂用組成物 |
| US7129278B2 (en) * | 2000-02-17 | 2006-10-31 | The Sherwin-Williams Company | Aqueous polymer dispersions |
| US6806314B2 (en) * | 2003-02-03 | 2004-10-19 | Ppg Industries Ohio, Inc. | Coating of Hydroxy-functional polymer(s), crosslinker, and 1,3- and 1,4-cyclohexane dimethanols |
| US6818293B1 (en) * | 2003-04-24 | 2004-11-16 | Eastman Chemical Company | Stabilized polyester fibers and films |
| US7425594B2 (en) * | 2005-11-23 | 2008-09-16 | Ppg Industries Ohio, Inc. | Copolymer of glycidyl ester and/or ether with polyol |
-
2009
- 2009-05-04 JP JP2011510550A patent/JP5390599B2/ja not_active Expired - Fee Related
- 2009-05-04 WO PCT/US2009/042643 patent/WO2009142898A1/en not_active Ceased
- 2009-05-04 CN CN200980118516.3A patent/CN102037049B/zh not_active Expired - Fee Related
- 2009-05-04 EP EP09751127A patent/EP2283060A1/en not_active Withdrawn
- 2009-05-04 US US12/989,495 patent/US20110040046A1/en not_active Abandoned
- 2009-05-21 TW TW098116880A patent/TW201002751A/zh unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI612125B (zh) * | 2013-12-18 | 2018-01-21 | Rohm And Haas Electronic Materials Llc | 可變換之波長轉換介質 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2283060A1 (en) | 2011-02-16 |
| JP5390599B2 (ja) | 2014-01-15 |
| WO2009142898A1 (en) | 2009-11-26 |
| CN102037049A (zh) | 2011-04-27 |
| JP2011521073A (ja) | 2011-07-21 |
| CN102037049B (zh) | 2014-09-03 |
| US20110040046A1 (en) | 2011-02-17 |
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