CN1374292A - Synthesis of anacardian amine as epoxy resin curing agent - Google Patents
Synthesis of anacardian amine as epoxy resin curing agent Download PDFInfo
- Publication number
- CN1374292A CN1374292A CN 02116454 CN02116454A CN1374292A CN 1374292 A CN1374292 A CN 1374292A CN 02116454 CN02116454 CN 02116454 CN 02116454 A CN02116454 A CN 02116454A CN 1374292 A CN1374292 A CN 1374292A
- Authority
- CN
- China
- Prior art keywords
- amine
- cashew nut
- curing agent
- anacardian
- temperature
- 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
- 150000001412 amines Chemical class 0.000 title claims abstract description 33
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 18
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 6
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 6
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 244000226021 Anacardium occidentale Species 0.000 claims abstract description 18
- 235000020226 cashew nut Nutrition 0.000 claims abstract description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000008098 formaldehyde solution Substances 0.000 claims abstract description 14
- 238000006683 Mannich reaction Methods 0.000 claims abstract description 3
- 239000004593 Epoxy Substances 0.000 claims description 15
- 230000018044 dehydration Effects 0.000 claims description 13
- 238000006297 dehydration reaction Methods 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 9
- 238000009413 insulation Methods 0.000 claims description 9
- 235000014571 nuts Nutrition 0.000 claims description 9
- 238000010189 synthetic method Methods 0.000 claims description 7
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 6
- 150000008431 aliphatic amides Chemical class 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 229960001124 trientine Drugs 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- -1 phenolic aldehyde Chemical class 0.000 claims description 2
- 238000001723 curing Methods 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 5
- 239000010466 nut oil Substances 0.000 abstract description 4
- 238000013035 low temperature curing Methods 0.000 abstract description 2
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000003368 amide group Chemical group 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 230000006837 decompression Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB021164541A CN1162395C (en) | 2002-04-05 | 2002-04-05 | Synthesis of anacardian amine as epoxy resin curing agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB021164541A CN1162395C (en) | 2002-04-05 | 2002-04-05 | Synthesis of anacardian amine as epoxy resin curing agent |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1374292A true CN1374292A (en) | 2002-10-16 |
CN1162395C CN1162395C (en) | 2004-08-18 |
Family
ID=4744114
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB021164541A Expired - Fee Related CN1162395C (en) | 2002-04-05 | 2002-04-05 | Synthesis of anacardian amine as epoxy resin curing agent |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1162395C (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008539207A (en) * | 2005-04-29 | 2008-11-13 | シーカ・テクノロジー・アーゲー | Mannich base based on resorcinol |
CN101508856B (en) * | 2008-02-13 | 2011-04-13 | 上海涂料有限公司上海长风化工厂 | Cashew pnenolic aldehyde amine epoxide resin paint solidifying agent and method for producing the same |
CN101333286B (en) * | 2007-06-26 | 2011-08-17 | 上海经天新材料科技有限公司 | Amine epoxy curing agent modified by cardanol |
CN102898884A (en) * | 2012-09-26 | 2013-01-30 | 江苏三木集团有限公司 | Environment-friendly cashew amine epoxy curing agent for low volatile organic compound (VOC) anticorrosive coating and preparation method for curing agent |
CN102977670A (en) * | 2012-11-15 | 2013-03-20 | 江苏三木化工股份有限公司 | Cashew phenolic aldehyde amide epoxy hardener for four-season-general type anticorrosive paint and preparation method of cashew phenolic aldehyde amide epoxy hardener |
CN103254722A (en) * | 2013-04-07 | 2013-08-21 | 常州市武进燎原化工有限公司 | Special epoxy anticorrosion paint and preparation method thereof |
CN104736634A (en) * | 2012-10-31 | 2015-06-24 | 陶氏环球技术有限公司 | Curable epoxy resin composition |
US20190177472A1 (en) * | 2016-02-15 | 2019-06-13 | Sika Technology Ag | Curing agent for low-emission epoxy resin compositions |
CN111040566A (en) * | 2019-11-22 | 2020-04-21 | 山东齐鲁漆业有限公司 | Water-based epoxy anti-rust primer and preparation method thereof |
CN113416380A (en) * | 2021-05-21 | 2021-09-21 | 东莞爱的合成材料科技有限公司 | Resin composition and preparation method and application thereof |
CN114249881A (en) * | 2021-12-06 | 2022-03-29 | 浙江万盛股份有限公司 | Non-solvent cardanol aldehyde amine epoxy resin curing agent containing thiazole structure and preparation method thereof |
CN117024301A (en) * | 2023-06-09 | 2023-11-10 | 湖南聚仁化工新材料科技有限公司 | Modified fatty amine epoxy resin curing agent, preparation method thereof and epoxy resin cured product |
CN117362183A (en) * | 2023-10-10 | 2024-01-09 | 浙江万盛股份有限公司 | Cardanol modified Schiff base epoxy curing agent and preparation method thereof |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101173036B (en) * | 2006-11-03 | 2010-04-21 | 上海涂料有限公司上海长风化工厂 | Method for producing aquosity cashew shell liquid solidifying agent |
-
2002
- 2002-04-05 CN CNB021164541A patent/CN1162395C/en not_active Expired - Fee Related
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008539207A (en) * | 2005-04-29 | 2008-11-13 | シーカ・テクノロジー・アーゲー | Mannich base based on resorcinol |
CN101333286B (en) * | 2007-06-26 | 2011-08-17 | 上海经天新材料科技有限公司 | Amine epoxy curing agent modified by cardanol |
CN101508856B (en) * | 2008-02-13 | 2011-04-13 | 上海涂料有限公司上海长风化工厂 | Cashew pnenolic aldehyde amine epoxide resin paint solidifying agent and method for producing the same |
CN102898884B (en) * | 2012-09-26 | 2014-07-09 | 江苏三木集团有限公司 | Environment-friendly cashew amine epoxy curing agent for low volatile organic compound (VOC) anticorrosive coating and preparation method for curing agent |
CN102898884A (en) * | 2012-09-26 | 2013-01-30 | 江苏三木集团有限公司 | Environment-friendly cashew amine epoxy curing agent for low volatile organic compound (VOC) anticorrosive coating and preparation method for curing agent |
CN104736634A (en) * | 2012-10-31 | 2015-06-24 | 陶氏环球技术有限公司 | Curable epoxy resin composition |
CN102977670A (en) * | 2012-11-15 | 2013-03-20 | 江苏三木化工股份有限公司 | Cashew phenolic aldehyde amide epoxy hardener for four-season-general type anticorrosive paint and preparation method of cashew phenolic aldehyde amide epoxy hardener |
CN102977670B (en) * | 2012-11-15 | 2014-07-02 | 江苏三木化工股份有限公司 | Cashew phenolic aldehyde amide epoxy hardener for four-season-general type anticorrosive paint and preparation method of cashew phenolic aldehyde amide epoxy hardener |
CN103254722A (en) * | 2013-04-07 | 2013-08-21 | 常州市武进燎原化工有限公司 | Special epoxy anticorrosion paint and preparation method thereof |
US20190177472A1 (en) * | 2016-02-15 | 2019-06-13 | Sika Technology Ag | Curing agent for low-emission epoxy resin compositions |
US11279797B2 (en) * | 2016-02-15 | 2022-03-22 | Sika Technology Ag | Curing agent for low-emission epoxy resin compositions |
CN111040566A (en) * | 2019-11-22 | 2020-04-21 | 山东齐鲁漆业有限公司 | Water-based epoxy anti-rust primer and preparation method thereof |
CN113416380A (en) * | 2021-05-21 | 2021-09-21 | 东莞爱的合成材料科技有限公司 | Resin composition and preparation method and application thereof |
CN114249881A (en) * | 2021-12-06 | 2022-03-29 | 浙江万盛股份有限公司 | Non-solvent cardanol aldehyde amine epoxy resin curing agent containing thiazole structure and preparation method thereof |
CN114249881B (en) * | 2021-12-06 | 2023-09-26 | 浙江万盛股份有限公司 | Solvent-free cashew phenol aldehyde amine epoxy resin curing agent containing thiazole structure and preparation method thereof |
CN117024301A (en) * | 2023-06-09 | 2023-11-10 | 湖南聚仁化工新材料科技有限公司 | Modified fatty amine epoxy resin curing agent, preparation method thereof and epoxy resin cured product |
CN117024301B (en) * | 2023-06-09 | 2024-04-26 | 湖南聚仁新材料股份公司 | Modified fatty amine epoxy resin curing agent, preparation method thereof and epoxy resin cured product |
CN117362183A (en) * | 2023-10-10 | 2024-01-09 | 浙江万盛股份有限公司 | Cardanol modified Schiff base epoxy curing agent and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CN1162395C (en) | 2004-08-18 |
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Owner name: SHANGHAI MEIDONG BIOLOGICAL MATERIAL CO., LTD. Free format text: FORMER OWNER: CHANGCHUN INST. OF APPLIED CHEMISTRY, CHINESE ACADEMY OF SCIENCES Effective date: 20090904 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20090904 Address after: Room 328, No. 302 Edison Road, Shanghai, Pudong New Area Patentee after: Shanghai Meidong Biological Materials Co., Ltd. Address before: No. 159 Renmin Street, Jilin, Changchun Patentee before: Changchun Institue of Applied Chemistry, Chinese Academy of Sciences |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20040818 Termination date: 20160405 |
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CF01 | Termination of patent right due to non-payment of annual fee |