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
Abstract
The present invention is synthesis of anacardian amine as epoxy resin curing agent. Cashew nut oil, formaldehyde solution and alphatic amine as materials are made to generate Mannich reaction to produce natural long-chain substituted phenolic amion, i.e. said anacardian amine. As an epoxy resin curing agent, anacardian amine has good low temperature curing performance and fast curing speed. Unlike polyamide, which can not cure epoxy resin in temperature lower than 5 deg.c, anacardian amine can do at temperature as low as 0 deg.c. It has excellent flexibility, less toxicity, waterproof performance and chemical tolerance.
Description
Technical field: the synthetic method that the invention belongs to epoxy curing agent-cashew nut amine.
Background technology: because the Resins, epoxy raw material is easy to get, low price, the crosslinking curing thing has excellent mechanical property, electrical property, chemical resistance and outstanding many advantages such as adhesion property, make it have extremely widely and use, especially more general in the application of aspects such as tackiness agent, coating.In the application of Resins, epoxy, need use solidifying agent to be cured reaction with it, form three-dimensional netted three-dimensional arrangement after, just can demonstrate excellent performance.Most of solidifying agent except that catalysis class solidifying agent, its solidification process are after carrying out addition polymerization by solidifying agent and epoxy group(ing), to stay an important component part that becomes in the epoxy systems in the curable epoxide thing.It is for the molecular weight in the cross-linked network, form and cross-linking density, important influence, thus make mechanical property, thermostability and the chemical stability of curable epoxide thing, all can change because of the difference of solidifying agent.Therefore the research of various solidifying agent is the integral parts in the Resins, epoxy applied research.
The synthetic method that the purpose of this invention is to provide a kind of epoxy curing agent-cashew nut amine.
In the solidifying agent molecular structure that the present invention selects, contain aliphatic amide, phenyl, hydroxyl and long-chain substituting group.Aliphatic amide has been given under the normal temperature curing speed faster; Hydroxyl has katalysis for the open loop curing reaction of reactive hydrogen on the amido and epoxy group(ing), and this catalytic activity does not have obvious change yet when low temperature; Phenyl helps improving intensity; C on the phenyl ring
15The straight chain substituting group, fabulous hydrophobicity is arranged, the epoxy systems after make solidifying than other solidifying agent solidified epoxy systems, has stronger water tolerance and chemical-resistant to play toughening effect simultaneously.
This method is to be raw material with cashew nut shell oil, formaldehyde solution and aliphatic amide, and the natural long-chain that makes by mannich reaction (Mqnnich reaction) replaces phenolic aldehyde amine---be cashew nut amine.
Reaction formula is as follows:
Structure 1
Structure 2
Wherein: structure 1=90% structure 2=10%
In the formula, R:-CH
2-CH
2-
-CH
- 2-CH
- 2-CH
- 2-CH
- 2-CH
2-CH
2-
-(CH
2)
2-NH-(CH
2)
2-
-(CH
2)
2-NH-(CH
2)
2-NH-(CH
2)
2-
The cashew nut shell oil that adopts among the present invention: formaldehyde solution: aliphatic amide (mol ratio)=1.0～1.43: 0.7～1.1: 0.7～1.1;
Three steps of synthetic branch of cashew nut amine carry out:
The first step is got cashew nut shell oil in molar ratio, aliphatic dicarboxylic amine, specifically: quadrol, diamines, diethylenetriamine or triethylene tetramine; Drip the formaldehyde solution that purity is 36-37% then, under the nitrogen protection, temperature is controlled at 30-40 ℃, drips 1-1.5n;
In second step, heat up 80 ± 2 ℃ insulation 3-4h;
The 3rd step, underpressure distillation dehydration, temperature is controlled at 70-75 ± 2 ℃, and vacuum tightness 50-100mmHg finishes when dehydrating amount reaches theoretical amount 97%, and cooling discharge promptly gets epoxy curing agent-cashew nut amine.
The solidifying agent low-temperature curing performance that the present invention makes is good, and curing speed is fast, still can solidify in the time of 0 ℃, has overcome low-molecular-weight polyamide resin and has been difficult to below 10 ℃ solidify, can not the solidified shortcoming below 5 ℃.Have good snappiness and hypotoxicity, the solidification brittleness when having overcome polyamine and derivative cured epoxy resin thereof.Have excellent in water resistance and chemical resistant properties simultaneously, be better than low-molecular-weight polyamide resin and polyamine and derivative thereof.
Embodiment is as follows:
Embodiment 1:
On the reaction flask of a 500ml, agitator, condenser, thermometer, charging opening and ventpipe are housed.Drop into cashew nut shell oil 241.6g, stir, logical N
2Gas is given water of condensation.Drip quadrol 48g, temperature is controlled at 30 ℃, drips formaldehyde solution then, and purity is 37%, 65g, and temperature is controlled at 30 ℃, and the dropping time is 1.5h.Be warmed up to 80 ± 2 ℃ of insulation 4h again.Cool to 70+2 ℃, carry out decompression dehydration, vacuum tightness is 50mmHg, and theoretical dehydrating amount is 55g, and actual aquifer yield finishes when reaching 53g.Cooling discharge promptly gets product.
Amine value=300, reactive hydrogen equivalent=125 on the amido
Embodiment 2:
In device with example 1, drop into cashew nut shell oil 216g, stir logical N
2Gas is opened water of condensation.Drip the rare tetramine 75g of three second, temperature is controlled at 40 ℃, and dripping formaldehyde solution purity then is 37%, 40.5g, and temperature is controlled at 40 ℃, and the dropping time is 1h.Be warmed up to 80 ± 2 ℃ again, insulation 3.5h.Cool to 70+2 ℃, carry out decompression dehydration, vacuum tightness 50mmHg, theoretical dehydrating amount are 34.5g, and actual water outlet finishes when reaching 33.5g.Cooling discharge promptly gets product.
Amine value=378, reactive hydrogen equivalent=118 on the amido, yield 97%
Embodiment 3:
In device with example 1, drop into cashew nut shell oil 207g, stir logical N
2Gas is opened water of condensation.Drip quadrol 33g, temperature is controlled at 30 ℃.Drip formaldehyde solution then, purity is 36%, 45.8g, and temperature is controlled at 30 ℃, and the dropping time is 1h.Be warmed up to 80 ± 2 ℃ again, insulation 3.5h.Cool to 75 ± 2 ℃, carry out decompression dehydration, vacuum tightness is 100mmHg, and theoretical dehydrating amount is 38.3g, and actual dehydration side finishes when reaching 36.8g.Cooling discharge promptly gets product.
Amine value=250, reactive hydrogen equivalent=150 on the amido, yield=96%
Embodiment 4:
In device with example 1, drop into cashew nut shell oil 302g, stir logical N
2Gas is opened water of condensation.Drip quadrol 45g, temperature is controlled at 40 ℃.Drip formaldehyde solution then, purity is 37%, 61g, and temperature is controlled at 40 ℃, and the dropping time is 1.5h.Be warmed up to 80 ± 2 ℃ again, insulation 3.5h.Cool to 75 ± 2 ℃, carry out decompression dehydration, vacuum tightness is 100mmHg, and theoretical dehydrating amount is 56g, and actual dehydrating amount finishes when reaching 54.3g.Cooling discharge promptly gets product.
Amine value=235, reactive hydrogen equivalent=159 on the amido, yield=95%
Embodiment 5:
In device with example 1, drop into cashew nut oil 271.8g, stir logical N
2Gas is opened water of condensation.Drip hexanediamine 73.1g, temperature is controlled at 35 ℃.Drip formaldehyde solution then, purity is 37%, 51g, and temperature is controlled at 35 ℃, and the dropping time is 70 minutes.Be warmed up to 80 ± 2 ℃ again, insulation 4h.Cool to 75 ± 2 ℃, carry out decompression dehydration, vacuum tightness is 100mmHg, and theoretical dehydration is 48g, and actual dehydrating amount finishes when reaching 46.5g, and cooling discharge promptly gets product.
Amine value=200, reactive hydrogen equivalent=187 on the amido, yield=95%.
Embodiment 6:
In device with example 1, drop into cashew nut oil 189g, stir logical N
2Gas is opened water of condensation.Drip the rare triamine 51.5g of diethyl, temperature is controlled at 35 ℃.Drip formaldehyde solution then, purity is 37%, 40.5g, and temperature is controlled at 35 ℃, and the dropping time is 1h.Be warmed up to 80 ± 2 ℃ again, insulation 4h.Cool to 75 ± 2 ℃, carry out decompression dehydration, vacuum tightness is 100mmHg, and theoretical dehydration is 34.5g, and actual dehydrating amount finishes when reaching 33.5g, and cooling discharge promptly gets product.
Amine value=340, reactive hydrogen equivalent=124 on the amido, yield=96%.
Embodiment 7:
In device with example 1, drop into cashew nut oil 151g, stir logical N
2Gas is opened water of condensation.Drip the rare triamine 51.5g of diethyl, temperature is controlled at 40 ℃.Drip formaldehyde solution then, purity is 36%, 41.7g, and temperature is controlled at 40 ℃, and the dropping time is 1h.Be warmed up to 80 again
± 2℃, insulation 4h.Cool to 75
± 2℃, carry out decompression dehydration, vacuum tightness is 50mmHg, and theoretical dehydration is 35.7g, and actual dehydrating amount finishes when reaching 34.5g, and cooling discharge promptly gets product.
Amine value=400, reactive hydrogen equivalent=105 on the amido
Claims (5)
1. the synthetic method of an anacardian amine as epoxy resin curing agent is characterized in that with cashew nut shell oil, formaldehyde solution and aliphatic amide be raw material, and the natural long-chain that makes by mannich reaction replaces phenolic aldehyde amine-be cashew nut amine,
Structure 1
Structure 2 is wherein: in the structure 1=90% structure 2=10% formula, and R:-CH
2-CH
2-
-CH
- 2-CH
- 2-CH
- 2-CH
- 2-CH
2-CH
2-
-(CH
2)
2-NH-(CH
2)
2-
-(CH
2)
2-NH-(CH
2)
2-NH-(CH
2)
2-
The cashew nut shell oil that adopts among the present invention: formaldehyde solution: aliphatic amide (mol ratio)=1.0～1.43: 0.7～1.1: 0.7～1.1;
Three steps of synthetic branch of cashew nut amine carry out:
The first step is got cashew nut shell oil in molar ratio, aliphatic dicarboxylic amine, specifically: quadrol, diamines, diethylenetriamine or triethylene tetramine; Drip the formaldehyde solution that purity is 36-37% then, under the nitrogen protection, temperature is controlled at 30-40 ℃, drips 1-1.5n;
In second step, heat up 80 ± 2 ℃ insulation 3-4h;
The 3rd step, underpressure distillation dehydration, temperature is controlled at 70-75 ± 2 ℃, and vacuum tightness 50-100mmHg finishes when dehydrating amount reaches theoretical amount 97%, and cooling discharge promptly gets epoxy curing agent-cashew nut amine.
2. the synthetic method of epoxy curing agent as claimed in claim 1-cashew nut amine is characterized in that aliphatic dicarboxylic amine is quadrol.
3. the synthetic method of epoxy curing agent as claimed in claim 1-cashew nut amine is characterized in that aliphatic dicarboxylic amine is diamines.
4. the synthetic method of epoxy curing agent as claimed in claim 1-cashew nut amine is characterized in that aliphatic dicarboxylic amine is diethylenetriamine.
5. the synthetic method of epoxy curing agent as claimed in claim 1-cashew nut amine is characterized in that aliphatic dicarboxylic amine is triethylene tetramine.
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
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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 |
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| 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
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| 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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