Polyamine-substituted long-chain alkyl compounds, methods of making and methods of improving propellant performance
By adding polyamines to replace long-chain alkyl compounds as process aids in high-solids-content propellants, the problem of poor performance of existing process aids in high-solids-content propellants has been solved, and the fluidity and structural integrity of the propellant slurry have been improved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-11-21
- Publication Date
- 2026-03-03
AI Technical Summary
Existing process aids are not effective in high-solids-content propellant formulations and are difficult to meet the requirements of slurry process performance.
Adding polyamine-substituted long-chain alkyl compounds as process aids to solid propellants with a solid content of ≥90% can reduce viscosity and improve leveling properties. The specific preparation method includes dropwise addition of 2-hydroxyethyl acrylate and acrylonitrile under ice-salt bath conditions to obtain cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds.
It significantly improved the wetting state of the solid particles and binder system, reduced the yield value and viscosity of the slurry, increased the leveling index, and enhanced the fluidity and structural integrity of the slurry.
Smart Images

Figure QLYQS_1 
Figure QLYQS_2 
Figure BDA0004559738880000031
Abstract
Description
Technical Field
[0001] This invention belongs to the field of solid propellant technology, and relates to process aids for solid propellants, specifically to a polyamine-substituted long-chain alkyl compound, its preparation method, and a method for improving propellant performance. Background Technology
[0002] Solid propellants are composite material systems composed of high-energy oxidizers, metallic fuels, binders, curing agents, plasticizers, and various functional materials (such as bonding agents, process aids, and combustion catalysts). Their manufacturing process mainly includes three steps: slurry mixing, casting, and curing. Among these, propellant mixing and casting are processes carried out while the slurry is in a flowing state. Key process parameters such as the slurry's viscosity, yield value, and leveling index directly affect the mixing and casting process, playing a decisive role in the propellant's structural integrity and the stability of its internal ballistic performance.
[0003] To improve the processing performance of propellant slurries, engineers in the field of solid propellants both domestically and internationally have improved the flowability and leveling properties of propellant slurries and extended their trial life by selecting appropriate process aids. These process aids mainly include: methyl stearate, methyl oleate, lecithin, British detergent, phosphorus-containing compounds, and amide compounds (or polymers). Among them, methyl stearate and methyl oleate were two early process aids used in HTPB propellants, playing a positive role in eliminating diluents and improving the processing performance of hydroxyl-terminated polybutadiene (HTPB) propellants. They are still used in various low-burning HTPB propellant formulations, but their effectiveness is poor in high-solids-content, high-burning formulations. Lecithin, composed of diglycerides of stearic acid, palmitic acid, and oleic acid linked to choline, is one of the earliest process aids used in propellants. It can improve the wettability of binders on the surface of ammonium perchlorate particles, thereby improving the processing performance of propellant slurries. British detergent, composed of ethyl oleate, pentaerythritol dioleate, and penetrant OT, is superior to lecithin in improving the wettability of the binder to ammonium perchlorate particles. However, the use of both lecithin and British detergent reduces the mechanical properties of the propellant to some extent. Phosphorus-containing compounds (including phosphine oxide and alkyl phosphates) can improve the mechanical properties of HTPB / IPDI propellants, but their effect is poor in HTPB / TDI propellants. Amide process aids, mainly including amide compounds and polyamides, have highly polar structures and readily migrate to the surface of ammonium perchlorate in the system, improving the interfacial properties between the binder and ammonium perchlorate. Although amide process aids can improve the process performance of HTPB propellant slurries, their effect is poor in high-solids-content propellant formulations with a solids content greater than 90%.
[0004] In recent years, with the increasing demand for high-solids-content composite solid propellants and the use of various new materials in propellant formulations, the excellent processing performance of propellant slurries has become increasingly important. However, existing process aids are insufficient to meet the processing performance requirements of high-solids-content propellant formulations. Therefore, to meet the processing performance requirements of high-solids-content propellants, it is urgent to develop process aids with superior performance. Summary of the Invention
[0005] In view of the defects and deficiencies of the existing technology, the purpose of this invention is to provide a method for preparing polyamine-substituted long-chain alkyl compounds and a method for improving propellant performance, thereby solving the technical problem that process aids in the prior art have poor application effects in high solid content propellant formulations with a solid content of ≥90%.
[0006] To solve the above-mentioned technical problems, the present invention adopts the following technical solution:
[0007] A method for improving propellant performance, the method comprising: adding a polyamine-substituted long-chain alkyl compound to a solid propellant with a solid content of ≥90% as an adjuvant to reduce the viscosity of the solid propellant slurry and improve its flowability; wherein the chemical structural formula of the polyamine-substituted long-chain alkyl compound is shown in Formula I:
[0008]
[0009] The present invention also has the following technical features:
[0010] Specifically, the amount of the polyamine-substituted long-chain alkyl compound added to the solid propellant is 0.05–0.1 wt.%.
[0011] Specifically, the solid propellant is composed of the following raw materials: hydroxyl-terminated polybutadiene, dioctyl sebacate, toluene diisocyanate, triphenylbismuth, iron acetylacetone, ammonium perchlorate, octogen, and aluminum powder.
[0012] Specifically, the solid propellant, by mass percentage, is composed of the following raw materials: 5-8% hydroxyl-terminated polybutadiene, 3-5% dioctyl sebacate, 0.3-0.5% toluene diisocyanate, 0.02-0.05% triphenylbismuth, 0.01-0.05% ferric acetylacetone, 20-30% ammonium perchlorate, 30-50% octogen, and 20-30% aluminum powder.
[0013] Specifically, the preparation method of the polyamine-substituted long-chain alkyl compound includes the following steps: N-oleo-1,3-propanediamine is added to a reaction vessel, and the mixture is cooled to 0-5°C under stirring conditions via an ice-salt bath. Then, 2-hydroxyethyl acrylate is added dropwise, maintaining the reaction temperature at 0-10°C. After the addition of 2-hydroxyethyl acrylate is complete, the temperature is raised to 40-60°C and kept constant for 1-2 hours. After the reaction is complete, the temperature is lowered to 0-5°C via an ice-salt bath, and then acrylonitrile is added dropwise, maintaining the reaction temperature at 0-10°C. After the addition of acrylonitrile is complete, the temperature is raised to 60-80°C and kept constant for 1-2 hours. After the reaction is complete, the resulting reaction product is distilled under reduced pressure to obtain the polyamine-substituted long-chain alkyl compound.
[0014] Specifically, the molar ratio of N-oleo-1,3-propanediamine to 2-hydroxyethyl acrylate is 1:1.
[0015] Specifically, the molar ratio of N-oleo-1,3-propanediamine to acrylonitrile is 1:1.
[0016] Specifically, the reaction vessel is a three-necked flask equipped with a mechanical stirrer, a thermometer, a constant-pressure dropping funnel, and an ice-salt bath.
[0017] This invention also protects polyamine-substituted long-chain alkyl compounds as described above.
[0018] The present invention also protects the preparation method of the polyamine-substituted long-chain alkyl compounds as described above.
[0019] The beneficial technical effects of this invention compared to the prior art are as follows:
[0020] The cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds of the present invention, when added at 0.05% to 0.1% in the formulation of composite solid propellants, can significantly improve the wetting state of the solid particles of the propellant and the binder system, making the solid particles easier to disperse, reducing the structural strength that hinders flow inside the slurry, lowering the yield value and viscosity of the slurry, and improving the leveling index of the slurry. This compound is well used as a process aid in solid propellants with a solid content of ≥90%.
[0021] The technical solution of the present invention will be further described below with reference to the embodiments. Detailed Implementation
[0022] It should be noted that, unless otherwise specified, all raw materials used in this invention are those known in the art.
[0023] Following the above technical solutions, specific embodiments of the present invention are given below. It should be noted that the present invention is not limited to the following specific embodiments, and all equivalent modifications made based on the technical solutions of this application fall within the protection scope of the present invention.
[0024] Example 1:
[0025] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. After cooling to 0°C under stirring conditions using an ice-salt bath, 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise, maintaining the reaction time... The reaction temperature was 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature was slowly raised to 60 °C and kept constant for 2 hours. After the reaction was complete, the temperature was lowered to 0 °C using an ice-salt bath, and then 8.17 g (0.154 mol) of acrylonitrile was slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile, the temperature was slowly raised to 80 °C and kept constant for 2 hours. After the reaction was complete, the resulting product was distilled under reduced pressure to obtain 74.9 g of a pale yellow, oily, transparent liquid, with a yield of 98.5%.
[0026] In this embodiment, the final pale yellow, oily, transparent liquid product was analyzed, and its characterization data are as follows:
[0027] Infrared spectroscopy (KBr, cm⁻¹) -1 ): 3101,3069,2869,2823,2732,1704,1598,1501,1423,1209,1181,957,886;
[0028] Elemental analysis (%): C 70.41, H 11.19, N 8.53;
[0029] 1H NMR spectrum 1 HNMR (400MHz, CDCl3, δ, ppm): 0.88s (3H, CH3), 1.26~1.36br. (24H, CH2), 1.5t (1H, NH), 2.16b r.(4H,CH2),2.36~3.01br.(12H,CH2),3.54~4.22dt(4H,CH2),4.89s(1H,OH),5.34q(2H,CH);
[0030] Carbon NMR Spectroscopy 13CNMR (400MHz, CDCl3, δ, ppm): 14.1, 17.1, 22.7, 27.3, 29.7, 31.9, 36.1, 46.3, 48.9, 51.7, 55.7, 61.1, 64.5, 119.5, 130.6, 171.2.
[0031] Hydroxyl value: 2.0124 mmol / g (theoretical value 2.0252 mmol / g).
[0032] Based on the above characterization data, the chemical structural formula of the product can be deduced as shown in Formula I:
[0033]
[0034] The compound is a cyano- and hydroxyl-modified N-polyamine-substituted long-chain alkyl compound, named (Z)-3-((3-((2-cyanoethyl)(octadecyl-9-en-1-yl)amino)propyl)amino)propionic acid 2-hydroxyethyl ester.
[0035] Example 2:
[0036] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. After cooling to 5 °C under stirring conditions using an ice-salt bath, 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise, maintaining the reaction time... The reaction temperature should be 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature is slowly raised to 40 °C and kept constant for 1 hour. After the reaction is complete, the temperature is lowered to 0 °C using an ice-salt bath, and then 8.17 g (0.154 mol) of acrylonitrile is slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile is complete, the temperature is slowly raised to 80 °C and kept constant for 2 hours. After the reaction is complete, the resulting product is distilled under reduced pressure to obtain 73.22 g of a pale yellow, oily, transparent liquid, with a yield of 96.3%.
[0037] In this embodiment, the final obtained pale yellow oily transparent liquid product was analyzed, and its characterization data were consistent with those of Example 1.
[0038] Example 3:
[0039] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. After cooling to 0 °C under stirring conditions using an ice-salt bath, 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise to maintain the reaction. The temperature was 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature was slowly raised to 50 °C and held at that temperature for 2 hours. After the reaction was complete, the temperature was lowered to 5 °C using an ice-salt bath, and then 8.17 g (0.154 mol) of acrylonitrile was slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile, the temperature was slowly raised to 60 °C and held at that temperature for 1 hour. After the reaction was complete, the resulting product was distilled under reduced pressure to obtain 72.39 g of a pale yellow, oily, transparent liquid, with a yield of 95.2%.
[0040] In this embodiment, the final obtained pale yellow oily transparent liquid product was analyzed, and its characterization data were consistent with those of Example 1.
[0041] Example 4:
[0042] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. The mixture is then cooled to 5 °C under stirring conditions using an ice-salt bath. 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise while maintaining the reaction time... The reaction temperature was 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature was slowly raised to 60 °C and kept constant for 1 hour. After the reaction was complete, the temperature was lowered to 5 °C using an ice-salt bath, and 8.17 g (0.154 mol) of acrylonitrile was slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile, the temperature was slowly raised to 60 °C and kept constant for 1 hour. After the reaction was complete, the resulting product was distilled under reduced pressure to obtain 73.84 g of a pale yellow, oily, transparent liquid, with a yield of 97.1%.
[0043] In this embodiment, the final obtained pale yellow oily transparent liquid product was analyzed, and its characterization data were consistent with those of Example 1.
[0044] Example 5:
[0045] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. After cooling to 0°C under stirring conditions using an ice-salt bath, 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise, maintaining the reaction time... The reaction temperature was 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature was slowly raised to 40 °C and kept constant for 2 hours. After the reaction was complete, the temperature was lowered to 5 °C using an ice-salt bath, and 8.17 g (0.154 mol) of acrylonitrile was slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile, the temperature was slowly raised to 80 °C and kept constant for 2 hours. After the reaction was complete, the resulting product was distilled under reduced pressure to obtain 74.37 g of a pale yellow, oily, transparent liquid, with a yield of 97.8%.
[0046] In this embodiment, the final obtained pale yellow oily transparent liquid product was analyzed, and its characterization data were consistent with those of Example 1.
[0047] Example 6:
[0048] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. After cooling to 0 °C under stirring conditions using an ice-salt bath, 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise to maintain the reaction. The temperature was 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature was slowly raised to 40 °C and held at that temperature for 2 hours. After the reaction was complete, the temperature was lowered to 0 °C using an ice-salt bath, and then 8.17 g (0.154 mol) of acrylonitrile was slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile, the temperature was slowly raised to 70 °C and held at that temperature for 1 hour. After the reaction was complete, the resulting product was distilled under reduced pressure to obtain 73.68 g of a pale yellow, oily, transparent liquid, with a yield of 96.9%.
[0049] In this embodiment, the final obtained pale yellow oily transparent liquid product was analyzed, and its characterization data were consistent with those of Example 1.
[0050] Example 7:
[0051] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. The mixture is then cooled to 5 °C under stirring conditions using an ice-salt bath. 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise while maintaining the reaction time... The reaction temperature was 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature was slowly raised to 50 °C and kept constant for 1 hour. After the reaction was complete, the temperature was lowered to 5 °C using an ice-salt bath, and 8.17 g (0.154 mol) of acrylonitrile was slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile, the temperature was slowly raised to 70 °C and kept constant for 1 hour. After the reaction was complete, the resulting product was distilled under reduced pressure to obtain 74.06 g of a pale yellow, oily, transparent liquid, with a yield of 97.4%.
[0052] In this embodiment, the final obtained pale yellow oily transparent liquid product was analyzed, and its characterization data were consistent with those of Example 1.
[0053] Example 8:
[0054] This embodiment provides a method for preparing cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds. The method specifically includes the following steps: 50 g (0.154 mol) of N-oleo-1,3-propanediamine is added to a 100 mL three-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and ice-salt bath. The mixture is then cooled to 5 °C under stirring conditions using an ice-salt bath. 17.88 g (0.154 mol) of 2-hydroxyethyl acrylate is slowly added dropwise while maintaining the reaction time... The reaction temperature was 0–10 °C. After the addition of 2-hydroxyethyl acrylate, the temperature was slowly raised to 40 °C and kept constant for 2 hours. After the reaction was completed, the temperature was lowered to 5 °C by an ice-salt bath, and 8.17 g (0.154 mol) of acrylonitrile was slowly added dropwise while maintaining the reaction temperature at 0–10 °C. After the addition of acrylonitrile, the temperature was slowly raised to 80 °C and kept constant for 2 hours. After the reaction was completed, the resulting reaction product was distilled under reduced pressure to obtain 73.52 g of a pale yellow, oily, transparent liquid, with a yield of 96.7%.
[0055] In this embodiment, the final obtained pale yellow oily transparent liquid product was analyzed, and its characterization data were consistent with those of Example 1.
[0056] Example 9:
[0057] This embodiment provides a method for improving propellant performance using cyano and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds prepared in Examples 1 to 8. The specific process of this method is as follows: 0.05 to 0.1 wt.% of polyamine-substituted long-chain alkyl compounds are added to a solid propellant with a solid content of 90% as a process aid to reduce the viscosity of the solid propellant slurry and improve the leveling properties of the solid propellant slurry.
[0058] In this embodiment, the curing conditions used for testing process performance were: curing time 180 h, curing temperature 50 °C. The basic formulation of the solid propellant is shown in Table 1.
[0059] Table 1. Solid Propellant Formulation Composition
[0060]
[0061] Verification of the effect of Example 9:
[0062] The following results were obtained after adding 0.05–0.1 wt.% of cyano- and hydroxyl-modified N-polyamine-substituted long-chain alkyl compounds to the solid propellant formulations with a solid content of 90% shown in Table 1: The solid propellant with added polyamine-substituted long-chain alkyl process aids had a falling ball viscosity range of 393 Pa·s to 420 Pa·s after 1 hour, a falling ball viscosity range of 1044 Pa·s to 1185 Pa·s after 6 hours, and a slurry leveling index range of 1.62–2.03. Compared with the solid propellant without added polyamine-substituted long-chain alkyl process aids, the falling ball viscosity decreased by 1.41–7.74% after 1 hour, decreased by 7.64–18.63% after 6 hours, and the slurry leveling index increased by 44.64–81.25%. The above results demonstrate that using cyano- and hydroxyl-modified N-polyamines to replace long-chain alkyl compounds as process aids for solid propellants can significantly reduce slurry viscosity and significantly improve slurry leveling properties.
Claims
1. A method for improving propellant performance, characterized in that, The method includes adding polyamine-substituted long-chain alkyl compounds to a solid propellant with a solid content of ≥90% as an adjuvant to reduce the viscosity of the solid propellant slurry and improve its flowability; The chemical structural formula of the polyamine-substituted long-chain alkyl compound is shown in Formula I: Formula I; The amount of the polyamine-substituted long-chain alkyl compound added to the solid propellant is 0.05–0.1 wt.%. The solid propellant is composed of the following raw materials: hydroxyl-terminated polybutadiene, dioctyl sebacate, toluene diisocyanate, triphenylbismuth, iron acetylacetone, ammonium perchlorate, octogen, and aluminum powder.
2. The method for improving propellant performance as described in claim 1, characterized in that, The solid propellant, by mass percentage, is composed of the following raw materials: 5-8% hydroxyl-terminated polybutadiene, 3-5% dioctyl sebacate, 0.3-0.5% toluene diisocyanate, 0.02-0.05% triphenylbismuth, 0.01-0.05% ferric acetylacetone, 20-30% ammonium perchlorate, 30-50% octogen, and 20-30% aluminum powder.
3. The method for improving propellant performance as described in claim 1, characterized in that, The preparation method of the polyamine-substituted long-chain alkyl compound specifically includes the following steps: N-oleo-1,3-propanediamine is added to a reaction vessel, and the mixture is cooled to 0-5°C under stirring conditions via an ice-salt bath. Then, 2-hydroxyethyl acrylate is added dropwise, maintaining the reaction temperature at 0-10°C. After the addition of 2-hydroxyethyl acrylate is complete, the temperature is raised to 40-60°C and the reaction is held at this temperature for 1-2 hours. After the reaction is complete, the temperature is lowered to 0-5°C via an ice-salt bath, and then acrylonitrile is added dropwise, maintaining the reaction temperature at 0-10°C. After the addition of acrylonitrile is complete, the temperature is raised to 60-80°C and the reaction is held at this temperature for 1-2 hours. After the reaction is complete, the resulting reaction product is distilled under reduced pressure to obtain the polyamine-substituted long-chain alkyl compound.
4. The method for improving propellant performance as described in claim 3, characterized in that, The molar ratio of N-oleo-1,3-propanediamine to 2-hydroxyethyl acrylate is 1:
1.
5. The method for improving propellant performance as described in claim 4, characterized in that, The molar ratio of N-oleo-1,3-propanediamine to acrylonitrile is 1:
1.
6. The method for improving propellant performance as described in claim 3, characterized in that, The reaction vessel is a three-necked flask equipped with a mechanical stirrer, a thermometer, a constant-pressure dropping funnel, and an ice-salt bath.
7. A polyamine-substituted long-chain alkyl compound, characterized in that, The chemical structural formula of the polyamine-substituted long-chain alkyl compound is shown in Formula I: Formula I.
8. A method for preparing a polyamine-substituted long-chain alkyl compound as described in claim 7, characterized in that, The method specifically includes the following steps: N-oleo-1,3-propanediamine is added to a reaction vessel, and the mixture is cooled to 0–5°C under stirring conditions via an ice-salt bath. Then, 2-hydroxyethyl acrylate is added dropwise, maintaining the reaction temperature at 0–10°C. After the addition of 2-hydroxyethyl acrylate is complete, the temperature is raised to 40–60°C and maintained for 1–2 hours. After the reaction is complete, the temperature is lowered to 0–5°C via an ice-salt bath, and then acrylonitrile is added dropwise, maintaining the reaction temperature at 0–10°C. After the addition of acrylonitrile is complete, the temperature is raised to 60–80°C and maintained for 1–2 hours. After the reaction is complete, the resulting reaction product is distilled under reduced pressure to obtain a polyamine-substituted long-chain alkyl compound.
Citation Information
Patent Citations
Amide-type aid and preparation method thereof
CN102320906A
Amide aid for composite solid propellant and synthesis method of amide aid
CN107628969A