CN101407708A - High temperature resistant, high strength modified epoxy resin adhesive and preparation thereof - Google Patents
High temperature resistant, high strength modified epoxy resin adhesive and preparation thereof Download PDFInfo
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- CN101407708A CN101407708A CNA2008101431485A CN200810143148A CN101407708A CN 101407708 A CN101407708 A CN 101407708A CN A2008101431485 A CNA2008101431485 A CN A2008101431485A CN 200810143148 A CN200810143148 A CN 200810143148A CN 101407708 A CN101407708 A CN 101407708A
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Abstract
The invention discloses a high-temperature-resistant and high-strength modified epoxy resin structured adhesive. First, polyether diols and 2, 4-tolylene diisocyanate are reacted to prepare polyurethane prepolymer (PUP); 1, 4-butanediol and trimethylolpropane are added into the prepared PUP and, after agitation, the mixture is added into TDE-85/E-51 epoxy resin; then, a curing agent is added into the TDE-85/E-51 epoxy resin and, and finally, a curing accelerator is added. The prepared adhesive has high tenacity, excellent high-temperature resistance and high reaction activity. After curing, the tensile and shear strength of the adhesive reach 22.81MPa at room temperature and 12.85MPa at high temperature of 160 DEG C, and the peel strength reaches 51.68N/cm, therefore, the adhesive can be widely applied to the adhesion of metals, porcelain, plastics and wood and the like.
Description
Technical field
The present invention relates to the synthetic and manufacture field of macromolecular material, be specifically related to a kind of high temperature resistant, high-strength polyurethane modified epoxide resin adhesive and preparation method thereof.
Background technology
Epoxyn is that a kind of adhesiveproperties is fine, uses very general tackiness agent, has obtained widespread use by Resins, epoxy synthetic tackiness agent in fields such as space flight, aviation, machinery, electronics, medical treatment.It is relatively poor that but Resins, epoxy exists toughness, and cured article fragility is big, and shock-resistance and vibratility are poor, defectives such as easy cracking.As the tackiness agent of the bonding usefulness of structure, must carry out the modified toughened of necessity to Resins, epoxy, could satisfy its special technique processing requirement.Present epoxy resin roughening technology has many kinds, is that the elastic body toughening technology of representative is the most significant epoxy resin roughening technology of toughening effect with urethane and paracril wherein.(Synthesis，characterization?and?applications?of?polyurethanearyl?cyanate?ester?resin，High?Performance?Polymers，2007，19(1)：97-112)。
Adopt polyurethane modified epoxy resin synthetic tackiness agent, though the intensity and the toughness of tackiness agent are greatly improved, but the improvement of its resistance toheat is still not enough, is difficult to satisfy simultaneously the high request of some high-tech sectors to over-all propertieies such as material high thermal resistance and intensity, toughness.
Summary of the invention
The present invention has overcome the shortcoming of gluing fragility of general Resins, epoxy and heat resistance difference, is suitable for the preparation of resistant to elevated temperatures high-strength high-toughness epoxy resin adhesive.The tackiness agent of preparation has the application performance of high-strength and high ductility, and the resistance to elevated temperatures excellence.
The objective of the invention is to realize by following manner:
Tackiness agent of the present invention is formulated by 100: 25: 3 mass ratio by polyurethane modified epoxy resin and solidifying agent and curing catalyst; Described polyurethane modified epoxy resin is made by urethane and Resins, epoxy reaction, and wherein the mass ratio of urethane and Resins, epoxy is 15～20: 75～80; Described urethane is to make base polyurethane prepolymer for use as (PUP) by polyether Glycols and 2,4 toluene diisocyanate reaction, adds 1 then, and 4-butyleneglycol and TriMethylolPropane(TMP) reaction obtain; What Resins, epoxy was selected for use is TDE-85 and E-51 blending epoxy; It is 1000 that polyether Glycols is selected from molecular weight.
The present invention is in conjunction with the advantage of TDE-85 resin and E-51 resin, adopt urethane that TDE-85 and E-51 blending epoxy are carried out toughening modifying, select the solidifying agent of the mixed aromatic diamine of Good Heat-resistance for use, improved snappiness, resistance to impact shock and the resistance toheat etc. of tackiness agent as tackiness agent.
The contriver is by discovering that TDE-85 and the most preferred mass ratio of E-51 blending epoxy are 1: 1.
Wherein the preferred mass percent of polyether Glycols and 2,4 toluene diisocyanate is 500: 170～175.
Base polyurethane prepolymer for use as and 1, the 4-butyleneglycol (1,4-BDO) and the preferred mass ratio of TriMethylolPropane(TMP) (TMP) be 1075～1080: 27: 9.
Solidifying agent is formed by mixing aromatic amine, and described mixing aromatic amine is selected from mphenylenediamine and diaminodiphenyl-methane.
The preferred mass percent of mphenylenediamine and diaminodiphenyl-methane is 1: 1.
Described curing catalyst is preferably 2-ethyl-4-methylimidazole.
Preparation method of the present invention is, polyether Glycols is heated to 110-130 ℃ of reflux dewatering 0.5-1.5h, is cooled to 50-55 ℃, add 2,4 toluene diisocyanate, slowly be warming up to 65-75 ℃, insulation also at the uniform velocity stirring reaction 1.5-2.5 hour obtains base polyurethane prepolymer for use as; In the base polyurethane prepolymer for use as for preparing, add 1,4-butyleneglycol and TriMethylolPropane(TMP) reaction obtain urethane, with the urethane that obtains after stirring, add in the blending epoxy of TDE-85 and E-51, stirring and insulation are 0.5-2 hour under 90-110 ℃ of condition, get polyurethane modified epoxy resin; Get solidifying agent, polyurethane modified epoxy resin, curing catalyst mixing, solidify.
Polyether Glycols is heated to 120 ℃ of reflux dewatering 1h, is cooled to 50 ℃; Add 2,4 toluene diisocyanate, slowly be warming up to 70 ℃, insulation and stirring reaction 2 hours at the uniform velocity.
After stirring, with solidifying agent, curing catalyst adds in the blending epoxy of TDE-85 and E-51 together with the urethane that obtains, stirs under 100 ℃ of conditions and is incubated 1 hour.
Described curing is after solidifying 10-15 hour under the 20-30 ℃ of condition, solidifies 1.5-3 hour down at 120-160 ℃ again.
Specific implementation process of the present invention is:
A. the preparation of base polyurethane prepolymer for use as
Polyether Glycols (it is 1000 that polyether Glycols is selected from molecular weight) is added in the four-hole boiling flask of a clean dried by said ratio, stir, be heated to 120 ℃ of reflux dewatering 1h, be cooled to 50 ℃ and add certain stoichiometric 2, the 4-tolylene diisocyanate, slowly be warming up to 70 ℃ again, insulation is also at the uniform velocity stirred, and stopped reaction to the required time promptly obtains base polyurethane prepolymer for use as.
B. the preparation of high-strength high-ductility thermostable polyurethane toughened epoxy resin adhesive
Add 1 in proportion in the base polyurethane prepolymer for use as for preparing, 4-butyleneglycol and TriMethylolPropane(TMP) add in TDE-85 and the E-51 blending epoxy after stirring together.Reaction is 1 hour under 100 ℃ of conditions.Aromatic amine curing agent mphenylenediamine and diaminodiphenyl-methane are pressed certain mass than mixing, after 15 minutes, be cooled to room temperature and make supercooled liquid 110 ℃ of insulations.At room temperature solidifying agent is mixed with polyurethane-epoxy resin, add 2-ethyl-4-methylimidazole promotor again, be prepared into the polyurethane modified epoxy resin tackiness agent.
The present invention also has following technical characterictic:
1, adopts the resin matrix of the blending epoxy of E-51 resin and TDE-85, make tackiness agent have the shock resistance of high-strength and high ductility, and possess outstanding high temperature resistance as tackiness agent.
2, adopt urethane that Resins, epoxy is carried out toughening modifying, improved tensile shear strength, impelling strength and the stripping strength of tackiness agent.
3, adopt mixed aromatic diamine (preferred especially mphenylenediamine and diaminodiphenyl-methane) as the solidifying agent of tackiness agent, make tackiness agent have lower solidification value and outstanding resistance toheat.
Tackiness agent toughness height of the present invention, resistance to elevated temperatures excellence, reactive behavior height.After the curing, the room temperature tensile shearing resistance of tackiness agent reaches 25.81MPa, and 160 ℃ of drawing by high temperature shearing resistances are 12.85MPa, and stripping strength reaches 51.68N/cm, can be widely used in bondings such as metal, pottery, plastics, timber.
Description of drawings
Fig. 1: TDE-85 Resins, epoxy and PUP, 1, the Infrared spectroscopy of 4-BDO and TMP reaction.
Fig. 2: E-51 Resins, epoxy and PUP, 1, the Infrared spectroscopy of 4-BDO and TMP reaction.
Fig. 3: tackiness agent thermogravimetric curve figure.
Embodiment
Following examples are intended to illustrate the present invention rather than limitation of the invention further.
Embodiment:
The preparation of base polyurethane prepolymer for use as: used polyether Glycols, number-average molecular weight 1000.The 50g polyether Glycols is added in the four-hole boiling flask of a clean dried, heat and continue stirring until 120 ℃ of reflux dewatering 1h, add 17.4g TDI after then it being cooled to 50 ℃, slowly be warming up to 70 ℃ again, insulation is also at the uniform velocity stirred, and reacts 2 hours.
The configuration of tackiness agent: in the base polyurethane prepolymer for use as for preparing, add 1.68g 1,4-butyleneglycol and 0.56g TriMethylolPropane(TMP), join 366.5g TDE-85 and E-51 after stirring again and mix in the Resins, epoxy of (mass ratio is 1: 1), reaction is 1 hour under 100 ℃ of conditions.Get each 54.52g of mphenylenediamine and diaminodiphenyl-methane, uniform mixing in beaker, is cooled to room temperature and makes supercooled liquid after 15 minutes 110 ℃ of insulations.At room temperature this supercooled liquid is mixed with polyurethane-epoxy resin at last, add 13.08g 2-ethyl-4-methylimidazole promotor again, promptly be prepared into the polyurethane modified epoxy resin tackiness agent.
Condition of cure: 25 ℃ solidify 12 hours after again 150 ℃ solidified 2 hours.
Through measuring, behind the fat adhesive solidification, the room temperature tensile shearing resistance reaches 25.81MPa, and 160 ℃ of drawing by high temperature shearing resistances are 12.85MPa, and stripping strength reaches 51.68N/cm.
Claims (11)
1, a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive is characterized in that, and is formulated by 100: 25: 3 mass ratio by polyurethane modified epoxy resin and solidifying agent and curing catalyst; Described polyurethane modified epoxy resin is made by urethane and Resins, epoxy reaction, and wherein the mass ratio of urethane and Resins, epoxy is 15～20: 75～80; Described urethane is to make base polyurethane prepolymer for use as by polyether Glycols and 2,4 toluene diisocyanate reaction, adds 1 then, and 4-butyleneglycol and TriMethylolPropane(TMP) reaction obtain; What Resins, epoxy was selected for use is TDE-85 and E-51 blending epoxy; It is 1000 that polyether Glycols is selected from molecular weight.
2, a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1 is characterized in that, TDE-85 and E-51 blending epoxy mass ratio are 1: 1.
3, a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1 is characterized in that wherein the mass percent of polyether Glycols and 2,4 toluene diisocyanate is 500: 170～175.
4, a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1 is characterized in that base polyurethane prepolymer for use as and 1, the mass ratio of 4-butyleneglycol and TriMethylolPropane(TMP) are 1075～1080: 27: 9.
5, a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1 is characterized in that, solidifying agent is formed by mixing aromatic amine, and described mixing aromatic amine is selected from mphenylenediamine and diaminodiphenyl-methane.
6, a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1 is characterized in that mphenylenediamine and diaminodiphenyl-methane mass percent are 1: 1.
7, a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1 is characterized in that described curing catalyst is a 2-ethyl-4-methylimidazole.
8, the method for preparing described a kind of high temperature resistant, the high-intensity Modified Epoxy Resin for Structural Adhesive of claim 1, it is characterized in that, polyether Glycols is heated to 110-130 ℃ of reflux dewatering 0.5-1.5h, be cooled to 50-55 ℃, add 2,4 toluene diisocyanate, slowly be warming up to 65-75 ℃, insulation also at the uniform velocity stirring reaction 1.5-2.5 hour obtains base polyurethane prepolymer for use as; In the base polyurethane prepolymer for use as for preparing, add 1,4-butyleneglycol and TriMethylolPropane(TMP) reaction obtain urethane, with the urethane that obtains after stirring, add in the blending epoxy of TDE-85 and E-51, stirring and insulation are 0.5-2 hour under 90-110 ℃ of condition, get polyurethane modified epoxy resin; Get solidifying agent, polyurethane modified epoxy resin, curing catalyst mixing, solidify.
9, the preparation method of a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1 is characterized in that polyether Glycols is heated to 120 ℃ of reflux dewatering 1h, is cooled to 50 ℃; Add 2,4 toluene diisocyanate, slowly be warming up to 70 ℃, insulation and stirring reaction 2 hours at the uniform velocity.
10, the preparation method of described a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1, it is characterized in that, with the urethane that obtains after stirring, with solidifying agent, curing catalyst adds in the blending epoxy of TDE-85 and E-51 together, stirs under 100 ℃ of conditions and is incubated 1 hour.
11, the preparation method of described a kind of high temperature resistant, high-intensity Modified Epoxy Resin for Structural Adhesive according to claim 1, it is characterized in that, described curing is after solidifying 10-15 hour under the 20-30 ℃ of condition, solidifies 1.5-3 hour down at 120-160 ℃ again.
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| CN101798380A (en) * | 2010-04-27 | 2010-08-11 | 哈尔滨工业大学 | Method for preparing high-strength high-toughness epoxy resin system |
| CN102127385A (en) * | 2010-12-30 | 2011-07-20 | 贵州云马飞机制造厂 | Special adhesive for adhering sample for measuring adhesive force of paint film coating and preparation method thereof |
| CN102391810A (en) * | 2011-09-19 | 2012-03-28 | 湖南神力铃胶粘剂制造有限公司 | Heat-resisting color-changing anti-counterfeiting epoxy adhesive and preparation method thereof |
| CN103865233A (en) * | 2014-03-28 | 2014-06-18 | 哈尔滨玻璃钢研究院 | Polyurethane modified blending resin matrix for heat-insulating support part and preparation method of matrix |
| CN105001383A (en) * | 2015-07-14 | 2015-10-28 | 合肥忠豪新材料有限公司 | High-strength resin die |
| CN105001824A (en) * | 2015-08-03 | 2015-10-28 | 中国工程物理研究院化工材料研究所 | Room temperature curing ultralow temperature epoxy sealant and preparation method thereof |
| CN105060768A (en) * | 2015-07-17 | 2015-11-18 | 东南大学 | Self-luminous anti-skidding pavement material and preparation method thereof |
| CN105086904A (en) * | 2015-09-11 | 2015-11-25 | 江苏振宇环保科技有限公司 | Preparation method of high-temperature-resistant epoxy structural adhesive |
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| CN108312281A (en) * | 2017-12-27 | 2018-07-24 | 中国林业科学研究院木材工业研究所 | A kind of preparation method of high flexibility high resiliency high grade of transparency timber film |
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2008
- 2008-09-05 CN CNA2008101431485A patent/CN101407708A/en active Pending
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| CN102127385A (en) * | 2010-12-30 | 2011-07-20 | 贵州云马飞机制造厂 | Special adhesive for adhering sample for measuring adhesive force of paint film coating and preparation method thereof |
| CN102127385B (en) * | 2010-12-30 | 2013-05-01 | 贵州云马飞机制造厂 | Special adhesive for adhering sample for measuring adhesive force of paint film coating and preparation method thereof |
| CN102391810A (en) * | 2011-09-19 | 2012-03-28 | 湖南神力铃胶粘剂制造有限公司 | Heat-resisting color-changing anti-counterfeiting epoxy adhesive and preparation method thereof |
| CN103865233B (en) * | 2014-03-28 | 2016-05-11 | 哈尔滨玻璃钢研究院 | Adiabatic polyurethane-modified blending resin matrix and preparation method thereof for supporting member |
| CN103865233A (en) * | 2014-03-28 | 2014-06-18 | 哈尔滨玻璃钢研究院 | Polyurethane modified blending resin matrix for heat-insulating support part and preparation method of matrix |
| CN105001383A (en) * | 2015-07-14 | 2015-10-28 | 合肥忠豪新材料有限公司 | High-strength resin die |
| CN105060768A (en) * | 2015-07-17 | 2015-11-18 | 东南大学 | Self-luminous anti-skidding pavement material and preparation method thereof |
| CN105001824A (en) * | 2015-08-03 | 2015-10-28 | 中国工程物理研究院化工材料研究所 | Room temperature curing ultralow temperature epoxy sealant and preparation method thereof |
| CN105001824B (en) * | 2015-08-03 | 2017-08-29 | 中国工程物理研究院化工材料研究所 | A kind of cold curing ultralow temperature epoxy sealing glue and preparation method thereof |
| CN105086904A (en) * | 2015-09-11 | 2015-11-25 | 江苏振宇环保科技有限公司 | Preparation method of high-temperature-resistant epoxy structural adhesive |
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| CN105646840B (en) * | 2016-04-01 | 2018-06-08 | 烟台德邦科技有限公司 | A kind of synthesis of polyester toughening type epoxy latent curing agent |
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| CN113322038A (en) * | 2021-06-28 | 2021-08-31 | 中国兵器工业第五九研究所 | Normal-temperature curing modified epoxy resin adhesive and preparation method thereof |
| CN114857409A (en) * | 2022-05-07 | 2022-08-05 | 山东非金属材料研究所 | Protective coating system for outer wall of high-risk pipeline |
| CN115011297A (en) * | 2022-07-15 | 2022-09-06 | 北京新风航天装备有限公司 | Adhesive for ceramic materials and preparation method thereof |
| CN115011297B (en) * | 2022-07-15 | 2023-01-20 | 北京新风航天装备有限公司 | Adhesive for ceramic material and preparation method thereof |
| CN115287031A (en) * | 2022-10-09 | 2022-11-04 | 建滔(广州)电子材料制造有限公司 | Temperature-resistant and aging-resistant epoxy resin and preparation method thereof |
| CN115287031B (en) * | 2022-10-09 | 2022-12-20 | 建滔(广州)电子材料制造有限公司 | Temperature-resistant and aging-resistant epoxy resin and preparation method thereof |
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Open date: 20090415 |