CN102675595A - 羟基酰胺型环氧树脂热潜在固化剂及其合成方法 - Google Patents
羟基酰胺型环氧树脂热潜在固化剂及其合成方法 Download PDFInfo
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- CN102675595A CN102675595A CN2012101157260A CN201210115726A CN102675595A CN 102675595 A CN102675595 A CN 102675595A CN 2012101157260 A CN2012101157260 A CN 2012101157260A CN 201210115726 A CN201210115726 A CN 201210115726A CN 102675595 A CN102675595 A CN 102675595A
- Authority
- CN
- China
- Prior art keywords
- epoxy resin
- curing agent
- oxyamide
- lactone
- type epoxy
- 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.)
- Granted
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 61
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 58
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 58
- 238000001308 synthesis method Methods 0.000 title abstract 3
- 150000002596 lactones Chemical class 0.000 claims abstract description 21
- 239000002798 polar solvent Substances 0.000 claims abstract description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 239000012044 organic layer Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000010025 steaming Methods 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000007142 ring opening reaction Methods 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- -1 aliphatics lactone Chemical class 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 150000007522 mineralic acids Chemical class 0.000 abstract description 2
- 238000003385 ring cleavage reaction Methods 0.000 abstract 2
- 230000002411 adverse Effects 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 238000009413 insulation Methods 0.000 abstract 1
- 238000005979 thermal decomposition reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010586 diagram Methods 0.000 description 22
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000002118 epoxides Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000001149 thermolysis Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000006399 behavior Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Epoxy Resins (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201210115726.0A CN102675595B (zh) | 2012-04-18 | 2012-04-18 | 羟基酰胺型环氧树脂热潜在固化剂及其合成方法 |
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CN201210115726.0A CN102675595B (zh) | 2012-04-18 | 2012-04-18 | 羟基酰胺型环氧树脂热潜在固化剂及其合成方法 |
Publications (2)
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CN102675595A true CN102675595A (zh) | 2012-09-19 |
CN102675595B CN102675595B (zh) | 2014-07-02 |
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CN201210115726.0A Expired - Fee Related CN102675595B (zh) | 2012-04-18 | 2012-04-18 | 羟基酰胺型环氧树脂热潜在固化剂及其合成方法 |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050119228A1 (en) * | 2000-09-19 | 2005-06-02 | Salvati Mark E. | Method for the preparation of fused heterocyclic succinimide compounds and analogs thereof |
WO2008045671A1 (en) * | 2006-10-06 | 2008-04-17 | Janssen Pharmaceutica, N.V. | Matrix metalloprotease inhibitors |
CN101379118A (zh) * | 2006-03-15 | 2009-03-04 | 株式会社艾迪科 | 预成型料用环氧树脂固化性组合物 |
-
2012
- 2012-04-18 CN CN201210115726.0A patent/CN102675595B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050119228A1 (en) * | 2000-09-19 | 2005-06-02 | Salvati Mark E. | Method for the preparation of fused heterocyclic succinimide compounds and analogs thereof |
CN101379118A (zh) * | 2006-03-15 | 2009-03-04 | 株式会社艾迪科 | 预成型料用环氧树脂固化性组合物 |
WO2008045671A1 (en) * | 2006-10-06 | 2008-04-17 | Janssen Pharmaceutica, N.V. | Matrix metalloprotease inhibitors |
Non-Patent Citations (2)
Title |
---|
《Macromolecules》 20030128 Fumio Sanda, et al. "A Novel Thermally Latent Anionic Initiator. Polymerization of Epoxide with Hydroxylamide Based on Thermal Dissociation" 第967-968页 1 第36卷, 第4期 * |
FUMIO SANDA, ET AL.: ""A Novel Thermally Latent Anionic Initiator. Polymerization of Epoxide with Hydroxylamide Based on Thermal Dissociation"", 《MACROMOLECULES》 * |
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CN102675595B (zh) | 2014-07-02 |
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Owner name: SHANGHAI WEIKAI PHOTOVOLTAIC NEW MATERIAL CO., LTD Free format text: FORMER NAME: WEIKAI CHEMICAL-PRODUCT CO., LTD., SHANGHAI |
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CP01 | Change in the name or title of a patent holder |
Address after: 201111 Shanghai city Minhang District Kunyang Road No. 2055 Patentee after: SHANGHAI WEIKAI OPTOELECTRONIC NEW MATERIALS CO., LTD. Patentee after: Shanghai Chengying New Materials Co., Ltd. Address before: 201111 Shanghai city Minhang District Kunyang Road No. 2055 Patentee before: Weikai Chemical-Product Co., Ltd., Shanghai Patentee before: Shanghai Chengying New Materials Co., Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee | ||
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Granted publication date: 20140702 Termination date: 20200418 |