CN105482078B - Rosin epoxy resin curing agent, its preparation method and application - Google Patents

Abstract

The invention discloses a rosin-based epoxy resin curing agent, which is selected from compounds having the structure shown in formula I: Wherein, R is an aliphatic segment. The invention also discloses a preparation method of the rosin-based epoxy resin curing agent, which is easy to implement, environmentally friendly and low in cost. The invention also discloses the application of the rosin-based epoxy resin curing agent, for example, mixing and curing the rosin-based epoxy resin curing agent and epoxy resin to form a cured product, which has excellent mechanical and thermal properties, and simultaneously The shape recovery rate is fast, the fixation rate and recovery rate are high, and the shape memory effect is good after repeated shape memory cycles, and can be widely used as a shape memory material.

Description

Rosin-based epoxy resin curing agent, its preparation method and application

technical field

The invention specifically relates to a rosin-based epoxy resin curing agent, its preparation method and application, such as application in shape memory, and belongs to the field of bio-based epoxy resin curing agents.

Background technique

Polymers with shape memory function include both thermoset shape memory polymers and thermoplastic shape memory polymers. Their difference is that the stationary phase of thermoplastic shape memory polymers is a physically cross-linked structure, while the stationary phase of thermosetting shape memory polymers is a chemically cross-linked structure. The shape recovery rate of thermoplastic shape memory polymers will decrease after repeated deformation recovery cycles, and its thermomechanical properties are difficult to meet the requirements of working under harsh environmental conditions. The shape memory polymer formed by epoxy resin and curing agent has been widely studied due to its characteristics of large recovery force, high shape fixation rate, easy adjustment of response temperature, excellent shape memory performance, and ability to work under harsh environmental conditions. And it has wide application prospects, especially in space deployable structures in aerospace.

At present, relevant researchers at home and abroad mainly focus on the research of bisphenol A shape memory epoxy resin. With the continuous research on epoxy resin shape memory materials, it is found that due to the structural characteristics of bisphenol A epoxy, it is necessary to introduce additional flexible components as shape memory materials, but it will not only lead to low material strength, poor heat resistance, and recovery. The stress is small, the recovery speed is slow, and the glass transition temperature range of the material is widened, thereby reducing the sensitivity to temperature. The introduction of particles, continuous fibers, etc. to form shape memory composites can improve the mechanical strength, modulus, recovery stress, etc., but the shape memory effect of the material, such as fracture strain and recoverable strain, will be sacrificed.

Contents of the invention

The main purpose of the present invention is to provide a rosin-based epoxy resin curing agent, its preparation method and application, to overcome the deficiencies in the prior art.

In order to realize the aforementioned object of the invention, the technical solutions adopted in the present invention include:

In some embodiments, a rosin-based epoxy resin curing agent is provided, which is selected from compounds having the structure shown in formula I:

Wherein, R is an aliphatic segment.

Further, R is selected from an alkyl segment containing -(CH ₂ ) _n -, n is an integer greater than or equal to 2, preferably 2 or 3.

In some embodiments, a preparation method of a rosin-based epoxy resin curing agent is provided, which includes: acrylopimaric acid dipropylene ester is mixed with a compound containing an amino group and a mercapto group in an organic solvent containing a photoinitiator, and making The formed mixed system is reacted under ultraviolet light irradiation, and then post-treated to obtain the rosin-based epoxy resin curing agent.

In some embodiments, a composition is provided, which includes the rosin-based epoxy resin curing agent and an epoxy resin that can cooperate with the rosin-based epoxy resin curing agent to form a cured product.

The epoxy resin may be selected from, but not limited to, any one or more of bisphenol A epoxy resin, diglycidyl terephthalate, and acrylic modified rosin-based epoxy resin.

In some embodiments, a cured product is provided, which is mainly formed by curing the composition.

In some embodiments, a method for preparing a cured product is provided, which includes: curing the composition at 80-100°C for 1-2 hours, 120-140°C for 1-2 hours, and 160-180°C for 2 hours. ~5h, the cured product was obtained.

In some embodiments, use of the cured product as a shape memory material is also provided.

Compared with the prior art, the advantages of the present invention include:

(1) With the bio-based material rosin as the starting raw material, a bio-based epoxy resin curing agent that is environmentally friendly, healthy and with simple preparation conditions has been prepared, wherein the curing agent is cured because the raw material rosin acid contains a phenanthrene ring Afterwards, it has good mechanical properties and thermal properties, and has a good application prospect.

(2) The preparation conditions of the rosin-based epoxy resin curing agent of the present invention are easy to implement, the preparation process is environmentally friendly, and the manufacturing cost is low.

(3) The present invention uses renewable rosin as a raw material, which provides a new approach for the deep processing of my country's rosin resources, is conducive to further exerting the economic value of rosin, and also opens up new raw materials and new approaches for the preparation of novel curing agents;

(4) The rosin-based epoxy resin curing agent of the present invention can be applied to the field of shape memory materials, as the cured product based on the rosin-based epoxy resin curing agent can be used as a shape memory material, and it has good thermal, mechanical and shape properties memory performance.

Description of drawings

Fig. 1 is the proton nuclear magnetic resonance spectrogram of the obtained rosin-based epoxy resin curing agent in embodiment 1.

detailed description

The invention mainly relates to a rosin-based epoxy resin curing agent, the raw material of which is rosin acid, which is biologically sourced, and the cured product formed by the curing agent has good performance.

One aspect of the present invention provides a rosin-based epoxy resin curing agent, which is selected from compounds with the structure shown in formula I:

Wherein, R is an aliphatic segment, preferably, R is selected from an alkyl segment containing -(CH ₂ ) _n -, n is an integer greater than or equal to 2, preferably 2 or 3.

Another aspect of the present invention provides a kind of preparation method of rosin-based epoxy resin curing agent, it comprises: propylene pimarate dipropylene ester is mixed with the compound containing amino group and mercapto group in the organic solvent containing photoinitiator, and The formed mixed system is reacted under ultraviolet light irradiation, and then the target product is obtained through post-treatment.

In a more specific embodiment, the preparation method includes: using abietic acid as raw material to add polymerization inhibitor hydroquinone and acrylic acid, obtain propylene pimaric acid through the reaction of Diels-Alder, and then utilize carboxyl and bromopropylene to react Prepare propylene pimarate dipropylene ester, and finally use the reaction of double bond and mercapto group to prepare rosin-based epoxy resin curing agent.

In a more specific embodiment, the preparation method comprises the following steps:

(1) preparation of propylene pimaric acid;

(2) preparation of propylene pimarate dipropylene;

(3) Preparation of rosin-based epoxy resin curing agent: adding dipropylene propylene mararate and a compound containing amino and mercapto groups into an organic solvent containing a photoinitiator, and then irradiating with ultraviolet light for reaction. After the reaction is finished, the product is washed, the solvent is removed, and the target product is obtained by drying.

The compound containing amino and mercapto groups is selected from NH ₂ -R-SH or their hydrochloride compounds, R is -(CH ₂ ) _n -, n is a positive integer greater than or equal to 2, preferably 2 or 3.

In some preferred embodiments, the mass ratio of the dipropylene propylene pimarate, the compound containing both amino and mercapto groups, and the photoinitiator is: 1:0.3-0.7:0.004-0.08.

Further, the organic solvent may be preferably selected from but not limited to one or more of dimethylformamide, 1,4-dioxane, ethanol, and tetrahydrofuran.

Further, the photoinitiator may preferably be selected from, but not limited to, one of benzoin dimethyl ether, camphorquinone, and benzophenone.

Wherein, the consumption of photoinitiator can be adjusted according to the raw material amount of reaction, is as the criterion that can initiate reaction, in order to play better catalytic effect while saving raw material, the consumption of photoinitiator is preferably propylene pimarate dipropylene ester 0.4% to 8% of the mass.

In some preferred embodiments, the reaction condition is to irradiate with ultraviolet light for 1-8 hours.

The propylene pimaric acid can be prepared in a manner known in the industry, such as the scheme disclosed in CN102977265A. For example, as one of the preferred schemes, the preparation method of propylene pimaric acid may include: under a protective atmosphere, mixing abietic acid, acrylic acid and a polymerization inhibitor hydroquinone, heating to 140-160°C for 1- 3h, then heated to 170-200°C for 4-15h, the obtained product was ultrasonically dissolved in diethyl ether, then added to petroleum ether 2-6 times the volume of diethyl ether for precipitation, and finally dried to obtain acrylpimaric acid.

More preferably, the mass ratio of the abietic acid, acrylic acid and hydroquinone is: 1:0.2-0.7:0.004-0.04.

Further, the protective atmosphere can be formed by one or more of nitrogen, argon, helium, etc., and nitrogen is preferred from the perspective of cost saving.

The dipropylene propylene pimarate can also be prepared by methods known in the industry, for example, by the scheme disclosed in CN102977265A. For example, as one of the preferred schemes, the preparation method of dipropylene propylene pimarate comprises: adding propylene pimaric acid, propylene bromide, and acid-binding agent potassium carbonate to an acetone solvent, stirring and reacting at 60-90°C for 12 After ~24h, the obtained product was washed, the organic phase was taken, and then dried to obtain dipropylene propylene pimarate.

More preferably, the mass ratio among the propylene pimaric acid, propylene bromide and potassium carbonate is: 1:1-2:0.5-1.5.

Another aspect of the present invention also provides the use of the rosin-based epoxy resin curing agent.

For example, a composition is provided in some embodiments, which includes the rosin-based epoxy resin curing agent and an epoxy resin that can cooperate with the rosin-based epoxy resin curing agent to form a cured product.

The epoxy resin may be at least selected from any one of bisphenol A epoxy resin, diglycidyl terephthalate, and acrylic modified rosin-based epoxy resin, but is not limited thereto.

In a more preferred embodiment, the composition consists of the following raw materials in parts by weight:

100 parts by weight of the rosin-based epoxy resin curing agent;

90-160 parts by weight of the epoxy resin.

For example, some embodiments also provide a cured product, which is mainly formed by curing the composition.

For example, in some embodiments, there is also provided a method for preparing the cured product, which includes: curing the composition at 80-100°C for 1-2 hours, 120-140°C for 1-2 hours, 160 Curing at ~180°C for 2-5 hours to obtain the cured product. The cured product has good mechanical, thermal and shape memory properties.

Therefore, correspondingly, in some embodiments, use of the cured product as a shape memory material is also provided.

Typical embodiments embodying the features and advantages of the present invention will be described in detail in the following description. It should be understood that the invention is capable of various changes in different embodiments without departing from the scope of the invention, and that the description and illustrations therein are illustrative in nature and not limiting. this invention.

Unless otherwise defined, all technical and scientific terms used in this specification have the same meaning as commonly understood by one of ordinary skill in the technical field of the invention. The terms used in the description of the present invention are only for the purpose of describing specific embodiments, and are not intended to limit the present invention.

Example 1

(1) Under the protection of nitrogen, mix 50 parts by weight of abietic acid, 10 parts by weight of acrylic acid and 2 parts by weight of hydroquinone as a polymerization inhibitor, heat to 140°C for 2 hours, and then heat to 170°C for 15 hours , the obtained product was ultrasonically dissolved in diethyl ether, then added to 6 times the volume of petroleum ether for precipitation, and finally dried to obtain acrylpimaric acid.

(2) 30 parts by weight of propylene pimaric acid, 60 parts by weight of propylene bromide, and 30 parts by weight of acid-binding agent potassium carbonate were added to the acetone solvent, stirred and reacted at 80° C. for 12 hours, the resulting product was washed, and the organic phase was taken. Then dry to obtain dipropylene propylene pimarate.

(3) 10 parts by weight of propylene pimarate dipropylene and 5 parts by weight of α-mercaptoethylamine hydrochloride are added to the N,N-dimethylformaldehyde containing 0.4 parts by weight of photoinitiator benzoin dimethyl ether amide solvent, and then irradiated with ultraviolet light for 4h. After the reaction is finished, the product is washed, solvent removed, and dried to obtain a rosin-based epoxy resin curing agent. The structural identification result of this rosin-based epoxy resin curing agent is shown in Figure 1, and its specific data are as follows: ¹ H-NMR (CDCl ₃ , ppm): 0.65, 1.13, 1.04, 1.26～2.03, 2.52, 3.70, 4.04～4.15, 5.32. Show that above-mentioned rosin-based epoxy resin has the structure shown in formula II:

Fully mix 100 parts by weight of the prepared rosin-based epoxy resin curing agent and 100 parts by weight of bisphenol A epoxy resin, and then cure in 100°C curing agent for 2 hours, 130°C for 2 hours, and 180°C for 2 hours to obtain a cured product , the flexural modulus of the cured product is 2460MPa, the flexural strength is 100MPa, the tensile modulus is 3144MPa, the tensile strength is 72MPa, the shape memory fixation rate is 98.8%, and the shape recovery rate is 99.0%. When the thermal weight loss mass is 5 %, the corresponding decomposition temperature is 314°C.

Example 2

(1) Under nitrogen protection, mix 50 parts by weight of abietic acid, 35 parts by weight of acrylic acid and 1 part by weight of inhibitor hydroquinone, heat to 160 °C for 1 hour, and then heat to 200 °C for 4 hours , the obtained product was ultrasonically dissolved in diethyl ether, then added to petroleum ether 4 times the volume of diethyl ether for precipitation, and finally dried to obtain acrylpimaric acid.

(2) 30 parts by weight of propylene pimaric acid, 30 parts by weight of propylene bromide, and 15 parts by weight of acid-binding agent potassium carbonate were added to the acetone solvent, stirred and reacted at 70°C for 18 hours, and the resulting product was washed, and the organic phase was taken. Then dry to obtain dipropylene propylene pimarate.

(3) 10 parts by weight of propylene pimarate dipropylene ester and 3 parts by weight of α-mercaptoethylamine are added to the 1,4-dioxane/ethanol solvent containing the photoinitiator benzophenone of 0.04 parts by weight , and then irradiated with ultraviolet light for 8 h. After the reaction, the product was washed, solvent removed, and dried to obtain a rosin-based epoxy resin curing agent. The structural identification data were as follows: ¹ H-NMR (CDCl ₃ , ppm): 0.65, 1.13, 1.04, 1.26-2.03, 2.52, 3.70 , 4.04~4.15, 5.32, consistent with Figure 1. It shows that the structure of the rosin-based epoxy resin curing agent is shown in formula II.

Fully mix the prepared 100 parts by weight of rosin-based epoxy resin curing agent and 90 parts by weight of diglycidyl terephthalate, and cure at 80°C for 2h, 120°C for 2h, and 160°C for 5h to obtain Cured product containing rosin-based epoxy resin curing agent. The obtained flexural modulus of the cured product containing rosin-based epoxy resin curing agent is 2448MPa, the flexural strength is 98MPa, the tensile modulus is 3136MPa, the tensile strength is 70MPa, the shape memory fixation rate is 98.4%, and the shape recovery rate is 98.5%, when the thermal weight loss mass is 5%, the corresponding decomposition temperature is 310°C.

Example 3

(1) Under nitrogen protection, mix 50 parts by weight of abietic acid, 25 parts by weight of acrylic acid and 0.2 parts by weight of hydroquinone as a polymerization inhibitor, heat to 150°C for 2 hours, and then heat to 180°C for 9 hours , the obtained product was ultrasonically dissolved in diethyl ether, then added to petroleum ether 2 times the volume of diethyl ether for precipitation, and finally dried to obtain acrylpimaric acid.

(2) 30 parts by weight of propylene pimaric acid, 45 parts by weight of propylene bromide, and 45 parts by weight of acid-binding agent potassium carbonate were added to the acetone solvent, stirred and reacted at 90° C. for 12 hours, the resulting product was washed, and the organic phase was taken. Then dry to obtain dipropylene propylene pimarate.

(3) 10 parts by weight of propylene pimarate dipropylene ester and 7 parts by weight of 3-mercapto-1-propanamine were added to THF solvent containing 0.8 parts by weight of photoinitiator camphorquinone, and then ultraviolet light was irradiated for 1 h. After the reaction, wash the product, remove the solvent, and dry to obtain a rosin-based epoxy resin curing agent. The structural identification data are as follows: ¹ H-NMR (CDCl ₃ , ppm): 0.65, 1.13, 1.04, 1.26-2.03, 2.52-2.63 , 2.89, 4.04~4.15, 5.32. Show that above-mentioned rosin-based epoxy resin has structure shown in formula III:

Fully mix the obtained 100 parts by weight of rosin-based epoxy resin curing agent and 160 parts by weight of acrylic acid-modified rosin-based epoxy resin, cure at 90°C for 2 hours, cure at 140°C for 1 hour, and cure at 170°C for 4 hours to obtain Cured product containing rosin-based epoxy resin curing agent. The obtained flexural modulus of the cured product containing rosin-based epoxy resin curing agent is 2350MPa, the flexural strength is 90MPa, the tensile modulus is 3200MPa, the tensile strength is 70MPa, the shape memory fixation rate is 98%, and the shape recovery rate is 99%, when the thermal weight loss mass is 5%, the corresponding decomposition temperature is 321°C.

Example 4

(1) Under the protection of nitrogen, mix 50 parts by weight of abietic acid, 20 parts by weight of acrylic acid and 0.5 parts by weight of hydroquinone as a polymerization inhibitor, heat to 145 ° C for 2 hours, and then heat to 190 ° C for 6 hours , the obtained product was ultrasonically dissolved in diethyl ether, then added to petroleum ether 5 times the volume of diethyl ether for precipitation, and finally dried to obtain acrylpimaric acid.

(2) 30 parts by weight of propylene pimaric acid, 39 parts by weight of propylene bromide, and 21 parts by weight of acid-binding agent potassium carbonate were added to the acetone solvent, stirred and reacted at 70° C. for 20 h, the resulting product was washed, and the organic phase was taken. Then dry to obtain dipropylene propylene pimarate.

(3) 10 parts by weight of propylene pimarate dipropylene and 4 parts by weight of α-mercaptoethylamine hydrochloride are added to the 1,4-dioxane containing 0.2 parts by weight of photoinitiator benzoin dimethyl ether solvent, and then irradiated with ultraviolet light for 5h. After the reaction, the product was washed, solvent removed, and dried to obtain a rosin-based epoxy resin curing agent. The structural identification results are shown in Figure 1, and the specific data are: ¹ H-NMR (CDCl ₃ , ppm): 0.65, 1.13, 1.04 , 1.26~2.03, 2.52, 3.70, 4.04~4.15, 5.32, consistent with Figure 1. It shows that the structure of the above-mentioned rosin-based epoxy resin curing agent is shown in formula II.

Fully mix the prepared 100 parts by weight of rosin-based epoxy resin curing agent and 110 parts by weight of bisphenol A epoxy resin, and obtain a rosin-containing resin after curing at 85°C for 2h, 125°C for 2h, and 165°C for 4h. Cured product of epoxy resin curing agent. The obtained flexural modulus of the cured product containing rosin-based epoxy resin curing agent is 2438MPa, the flexural strength is 96MPa, the tensile modulus is 3130MPa, the tensile strength is 71MPa, the shape memory fixation rate is 98.2%, and the shape recovery rate is 98.7%, when the thermal weight loss mass is 5%, the corresponding decomposition temperature is 311°C.

Example 5

(1) Under the protection of nitrogen, mix 50 parts by weight of abietic acid, 30 parts by weight of acrylic acid and 1.5 parts by weight of inhibitor hydroquinone, heat to 155°C for 1 hour, and then heat to 185°C for 8 hours. The obtained product was ultrasonically dissolved in diethyl ether, then added to 3 times the volume of petroleum ether for precipitation, and finally dried to obtain acrylpimaric acid.

(2) 30 parts by weight of propylene pimaric acid, 51 parts by weight of propylene bromide, and 39 parts by weight of acid-binding agent potassium carbonate were added to the acetone solvent, stirred and reacted at 75°C for 19 hours, and the resulting product was washed, and the organic phase was taken, Then dry to obtain dipropylene propylene pimarate.

(3) 10 parts by weight of propylene pimarate dipropylene and 6 parts by weight of 3-mercapto-1-propylamine are added to the N,N-dimethylformamide containing the photoinitiator benzophenone of 0.6 parts by weight /ethanol solvent, and then irradiated with ultraviolet light for 3h. After the reaction, the product was washed, solvent removed, and dried to obtain a rosin-based epoxy resin curing agent. The structural identification results were as follows: ¹ H-NMR (CDCl ₃ , ppm): 0.65, 1.13, 1.04, 1.26-2.03, 2.52-2.63 , 2.89, 4.04~4.15, 5.32. It shows that the structure of the above rosin-based epoxy resin curing agent is shown in formula III.

Fully mix the prepared 100 parts by weight of rosin-based epoxy resin curing agent and 130 parts by weight of bisphenol A epoxy resin, and obtain a rosin-containing resin after curing at 95°C for 2h, 135°C for 1h, and 175°C for 4h. Cured product of epoxy resin curing agent. The obtained cured product containing rosin-based epoxy resin curing agent has a flexural modulus of 2252MPa, a flexural strength of 86MPa, a tensile modulus of 3000MPa, a tensile strength of 64MPa, a shape memory fixation rate of 99.1%, and a shape recovery rate of 98.3%, when the thermal weight loss mass is 5%, the corresponding decomposition temperature is 307°C.

It should be understood that the described embodiments of the present invention are for exemplary purposes only, and are not intended to limit the protection scope of the present invention. Those skilled in the art can make various other replacements, changes and improvements within the scope of the present invention. Accordingly, the present invention is not limited to the above-described embodiments, but only by the claims.

Claims (18)

1. A rosin-based epoxy resin curing agent is characterized in that it is selected from compounds with structures shown in formula I: Wherein, R is an aliphatic segment. 2 . The rosin-based epoxy resin curing agent according to claim 1 , wherein R is selected from alkyl segments containing -(CH ₂ ) _n -, and n is an integer greater than or equal to 2. 3 . 3. rosin-based epoxy resin curing agent as claimed in claim 2, is characterized in that: n is 2 or 3. 4. a preparation method of rosin-based epoxy resin curing agent, it is characterized in that comprising: acrylopimaric acid dipropylene ester is mixed with the compound that contains amino group and mercapto group in the organic solvent that contains photoinitiator, and makes the mixing that forms The system reacts under ultraviolet light irradiation, and then undergoes post-treatment to obtain the rosin-based epoxy resin curing agent. 5. The preparation method according to claim 4, characterized in that: the compound containing amino and mercapto is selected from the hydrochloride compounds of NH ₂ -R-SH and/or NH ₂ -R-SH, and R is a compound containing An alkyl segment of -(CH ₂ ) _n -, n is an integer greater than or equal to 2. 6. the preparation method as claimed in claim 5 is characterized in that: n is 2 or 3. 7. The preparation method according to claim 4, wherein the photoinitiator comprises any one or a combination of two or more of benzoin dimethyl ether, camphorquinone and benzophenone. 8. The preparation method according to claim 4, characterized in that: said organic solvent comprises any one or both of N,N-dimethylformamide, 1,4-dioxane, ethanol, tetrahydrofuran more than one combination. 9 . The preparation method according to claim 4 , wherein the mass ratio of the dipropylene propylene pimarate, the compound containing the amino group and the mercapto group to the photoinitiator is 1:0.3-0.7:0.004-0.08. 10 . The method for preparing a rosin-based epoxy resin curing agent according to claim 4 , characterized in that it comprises: reacting the mixed system at room temperature for 1-8 hours under ultraviolet light irradiation. 11 . 11. the preparation method of rosin-based epoxy resin curing agent as claimed in claim 4, is characterized in that, described post-processing comprises washing product after reaction finishes, desolventizes, and drying obtains described rosin-based epoxy resin Operation of resin curing agent. 12. the preparation method of rosin-based epoxy resin curing agent as claimed in claim 4 is characterized in that comprising: under protective atmosphere, abietic acid, acrylic acid and polymerization inhibitor Hydroquinone are mixed, heated to 140～ React at 160°C for 1-3 hours, then heat to 170-200°C for 4-15 hours, dissolve the resulting product in ether, then add it to petroleum ether 2-6 times the volume of ether to precipitate, and then dry to obtain acrylopine acid, and then utilize propylene pimaric acid to obtain the propylene pimaric acid dipropylene ester. 13. A composition, characterized in that comprising the rosin-based epoxy resin curing agent according to any one of claims 1-3 and the epoxy resin that can cooperate with the rosin-based epoxy resin curing agent to form a cured product resin. 14. The composition according to claim 13, characterized in that: the composition comprises 100 parts by weight of the rosin-based epoxy resin curing agent and 90-160 parts by weight of the epoxy resin. 15. according to the composition described in claim 13 or 14, it is characterized in that: described epoxy resin comprises bisphenol A epoxy resin, terephthalic acid diglycidyl ether, in acrylic acid modified rosin base epoxy resin Any one or a combination of two or more. 16. A cured product, mainly formed by curing the composition according to claim 13, 14 or 15. 17. A method for preparing a cured product, characterized in that it comprises: taking the composition described in claim 13, 14 or 15 and curing it at 80-100°C for 1-2 hours, 120-140°C for 1-2 hours, and 160-140°C for 1-2 hours. Curing at 180° C. for 2 to 5 hours to obtain the cured product. 18. The use of the cured product according to claim 16 as a shape memory material.