CN112479796B - Liquid type modified urea speed reducing agent, preparation method and solid propellant - Google Patents

Liquid type modified urea speed reducing agent, preparation method and solid propellant Download PDF

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CN112479796B
CN112479796B CN202011492731.4A CN202011492731A CN112479796B CN 112479796 B CN112479796 B CN 112479796B CN 202011492731 A CN202011492731 A CN 202011492731A CN 112479796 B CN112479796 B CN 112479796B
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speed reducer
agent
modified urea
solid propellant
propellant
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CN112479796A (en
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徐爽
庞爱民
潘新洲
李尚文
李海涛
武卓
汪越
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Hubei Institute of Aerospace Chemical Technology
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    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06D—MEANS FOR GENERATING SMOKE OR MIST; GAS-ATTACK COMPOSITIONS; GENERATION OF GAS FOR BLASTING OR PROPULSION (CHEMICAL PART)
    • C06D5/00—Generation of pressure gas, e.g. for blasting cartridges, starting cartridges, rockets
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B23/00—Compositions characterised by non-explosive or non-thermic constituents
    • C06B23/007—Ballistic modifiers, burning rate catalysts, burning rate depressing agents, e.g. for gas generating
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B29/00—Compositions containing an inorganic oxygen-halogen salt, e.g. chlorate, perchlorate
    • C06B29/22—Compositions containing an inorganic oxygen-halogen salt, e.g. chlorate, perchlorate the salt being ammonium perchlorate
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B31/00—Compositions containing an inorganic nitrogen-oxygen salt
    • C06B31/28—Compositions containing an inorganic nitrogen-oxygen salt the salt being ammonium nitrate
    • C06B31/32—Compositions containing an inorganic nitrogen-oxygen salt the salt being ammonium nitrate with a nitrated organic compound
    • C06B31/44—Compositions containing an inorganic nitrogen-oxygen salt the salt being ammonium nitrate with a nitrated organic compound the compound being nitroglycerine
    • C06B31/48—Compositions containing an inorganic nitrogen-oxygen salt the salt being ammonium nitrate with a nitrated organic compound the compound being nitroglycerine with other explosive or thermic component
    • C06B31/50—Compositions containing an inorganic nitrogen-oxygen salt the salt being ammonium nitrate with a nitrated organic compound the compound being nitroglycerine with other explosive or thermic component the other component being a nitrated organic compound

Abstract

The invention relates to a liquid type modified urea speed reducing agent, a preparation method and a solid propellant containing the speed reducing agent, wherein the structural formula of the speed reducing agent is as follows: x2NCONX2(ii) a Wherein X is CnH2nCN or hydrogen, and at most two X are hydrogen, wherein n is 1-10; the liquid speed reducing agent provided by the invention has better dispersibility and speed reducing effect compared with common solid speed reducing agents, can simultaneously reduce the burning rate and the pressure index of a propellant, and has wide application prospect in the solid propellant.

Description

Liquid type modified urea speed reducing agent, preparation method and solid propellant
Technical Field
The invention belongs to the technical field of solid propellants, and relates to a liquid modified urea speed reducing agent, a preparation method and a solid propellant containing the speed reducing agent.
Background
With the continuous development of solid rocket propulsion technology, solid rocket engines put new requirements on the performance of solid propellants. In practical use, the solid rocket engines with different purposes have different requirements on the burning speed of the used propellant, and the booster engine usually needs to use a high-burning-speed propellant so as to rapidly provide the thrust required by takeoff and acceleration; the cruise engine needs low-burning-rate propellant to ensure that long-time and continuous stable thrust is provided.
The combustion rate of the oxidizer AP in the propellant is a core factor influencing the combustion rate of the propellant, and the reduction of the combustion rate of the propellant can be realized by a physical way or a chemical way. A common physical adjustment is to increase the AP particle size in a manner that does not alter the chemical mechanism of the thermal decomposition and combustion reactions of the propellant. However, the use of a large amount of coarse-grained AP can lead to unreasonable grain size distribution of the propellant, thereby causing poor flowability and leveling property of the propellant slurry and causing the density of the propellant to be reduced. The chemical approach is to change the AP thermal decomposition and combustion reaction mechanism by adding a speed reducer, thereby realizing the regulation of the combustion speed of the propellant.
The existing speed reducer is generally solid particles or powder, and researches show that AP decomposition usually starts from the surface, and the contact of the speed reducer and the AP surface can further inhibit the surface reaction of AP. Therefore, the speed reduction effect can be effectively improved by coating the AP with the speed reduction agent or nanocrystallizing the speed reduction agent, but the problems of difficult large-scale engineering application, high cost and the like exist, and the dosage of the speed reduction agent is generally more than 2%, which can bring adverse effects on the energy, the mechanical property, the preparation process and the like of the propellant.
Disclosure of Invention
The invention aims to overcome the defects and provides a liquid modified urea speed reducing agent, a preparation method and a solid propellant containing the speed reducing agent, wherein the speed reducing agent has the following structural formula:
X2NCONX2
wherein n is 1-10, X is CnH2nCN or hydrogen, and at most two X are hydrogen, compared with the common solid speed reducing agent, the modified urea speed reducing agent is liquid at normal temperature, has better dispersibility and speed reducing effect, and can simultaneously reduce the burning rate and the pressure index of the propellant.
In order to achieve the above purpose, the invention provides the following technical scheme:
a liquid modified urea speed reducer has a structural formula as follows:
X2NCONX2；
in the structural formula, X is CnH2nCN or hydrogen, and the number of the hydrogen contained is less than or equal to 2; cnH2nIn CN, n is 1 to 10.
Furthermore, the molecular weight of the speed reducer is 150-1200.
The preparation method of the liquid modified urea speed reducing agent comprises the following steps:
(1) dispersing nitrile halide and an acid-binding agent into dichloromethane under an ice bath condition, wherein the molar ratio of the nitrile halide to the acid-binding agent is 1: 1-1.5;
(2) adding urea into the solution obtained in the step (1), wherein the molar ratio of the urea to the nitrile halide is as follows: 1: 2-4.
(3) Adding deionized water to quench the reaction, extracting, and drying in vacuum to obtain the product.
Further, in the step (2), the reaction temperature is room temperature, and the reaction time is not less than 12 h.
Further, the nitrile halide is a halogen element monosubstitution of acetonitrile, propionitrile, butyronitrile, valeronitrile, capronitrile, heptanenitrile, octanenitrile, nonanenitrile or decanonitrile, and the halogen element is chlorine, bromine or iodine.
Further, the acid-binding agent is organic weak base; the acid-binding agent is pyridine or triethylamine.
The solid propellant is characterized in that the mass percentage of the liquid modified urea speed reducer is 0.50-4.00%.
The solid propellant comprises the following components in percentage by mass:
Figure BDA0002841177880000021
Figure BDA0002841177880000031
the functional auxiliary agent comprises a curing catalyst, an anti-aging agent, a bonding agent and a speed reducing agent; the speed reducer is the liquid modified urea speed reducer, and the mass percent of the speed reducer is 0.5-4%.
Further, the polyurethane adhesive is one or more of hydroxyl-terminated polybutadiene HTPB, polyaziridin glycidyl ether GAP, ethylene oxide-tetrahydrofuran copolyether PET or polyethylene glycol PEG; the plasticizer is one or more of dioctyl sebacate DOS, nitroglycerin NG, butanetriol trinitrate BTTN, triethylene glycol dinitrate TEGDN or diethylene glycol dinitrate DEGDN; the oxidant is one or more of ammonium perchlorate AP or ammonium dinitramide ADN; the nitramine explosive is one or more of hexogen RDX, octogen HMX or hexanitrohexaazaisowurtzitane CL-20; the combustion agent is aluminum powder Al; the curing agent is one or more of isophorone diisocyanate (IPDI), Toluene Diisocyanate (TDI), 1, 6-Hexamethylene Diisocyanate (HDI) or polyfunctional isocyanate (N-100).
Further, the curing catalyst is triphenyl bismuth TPB; the anti-aging agent is one or more of N-methyl p-nitroaniline MNA or 2-nitrodiphenylamine 2-NDPA; the bonding agent is tris (2-methylaziridine) phosphine oxide MAPO, triethanolamine TEA or neutral polymer bonding agent NPBA.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention firstly prepares the compound with the structural formula of X2NCONX2The liquid modified urea speed reducing agent effectively improves the dispersibility and the speed reducing effect of the speed reducing agent, and can simultaneously reduce the burning rate and the pressure index of the propellant.
(2) Compared with the existing speed reducing agent, the liquid modified urea speed reducing agent provided by the invention needs less dosage when obtaining the same speed reducing effect, and is beneficial to reducing the energy loss of the propellant.
(3) The liquid modified urea speed reducer provided by the invention has wide application prospect in a polyurethane propellant system represented by a hydroxyl-terminated propellant and a nitrate plasticized polyether propellant, and has strong practicability.
Drawings
FIG. 1 is an infrared spectrum of a liquid modified urea speed reducer BRS-1 provided in example 1 of the present invention;
FIG. 2 is an infrared spectrum of a liquid modified urea speed reducer BRS-2 provided in example 2 of the present invention;
Detailed Description
The features and advantages of the present invention will become more apparent and appreciated from the following detailed description of the invention.
The word "exemplary" is used exclusively herein to mean "serving as an example, embodiment, or illustration. Any embodiment described herein as "exemplary" is not necessarily to be construed as preferred or advantageous over other embodiments. While the various aspects of the embodiments are presented in drawings, the drawings are not necessarily drawn to scale unless specifically indicated.
The invention relates to a liquid type modified urea speed reducer, which has the structural formula:
X2NCONX2；
in the structural formula, X is CnH2nCN or hydrogen, and the number of the hydrogen contained is less than or equal to 2; cnH2nIn CN, n is 1 to 10.
Furthermore, the molecular weight of the speed reducer is 150-1200.
Furthermore, n is 1-4, and the content of alkane in the structure of the speed reducer is less in the range, so that the speed reducer can have a strong speed reducing effect.
A preparation method of a liquid modified urea speed reducer comprises the following reaction formula:
Figure BDA0002841177880000041
wherein R is1Is halogen element chlorine, bromine or iodine; r2Is CnH2nWherein n is 1-10.
The method comprises the following steps:
(1) dispersing nitrile halide and an acid-binding agent into dichloromethane under an ice bath condition, wherein the molar ratio of the nitrile halide to the acid-binding agent is 1: 1-1.5;
(2) adding urea into the solution obtained in the step (1), wherein the molar ratio of the urea to the nitrile halide is as follows: 1: 2-4.
(3) Adding deionized water to quench the reaction, extracting, and drying in vacuum to obtain the product.
Further, in the step (2), the reaction temperature is room temperature, and the reaction time is more than or equal to 12 hours.
Further, the nitrile halide is a halogen element monosubstitution of acetonitrile, propionitrile, butyronitrile, valeronitrile, capronitrile, heptanenitrile, octanenitrile, nonanenitrile or decanonitrile, and the halogen element is chlorine, bromine or iodine.
Further, the acid-binding agent is an organic weak base, and pyridine or triethylamine is preferred.
The solid propellant comprises the liquid modified urea speed reducing agent, and the mass percentage of the liquid modified urea speed reducing agent is 0.50-4.00%, preferably 0.50-2.00% of the solid propellant.
The solid propellant comprises the following components in percentage by mass:
Figure BDA0002841177880000051
the functional auxiliary agent comprises a curing catalyst, an anti-aging agent, a bonding agent and a speed reducing agent; the speed reducer is the liquid modified urea speed reducer, and the mass percent of the speed reducer is 0.5-4%.
Further, the polyurethane adhesive is one or more of hydroxyl-terminated polybutadiene HTPB, polyaziridin glycidyl ether GAP, ethylene oxide-tetrahydrofuran copolyether PET or polyethylene glycol PEG;
the plasticizer is one or more of dioctyl sebacate DOS, nitroglycerin NG, butanetriol trinitrate BTTN, triethylene glycol dinitrate TEGDN or diethylene glycol dinitrate DEGDN;
the oxidant is one or more of ammonium perchlorate AP or ammonium dinitramide ADN;
the nitramine explosive is one or more of hexogen RDX, octogen HMX or hexanitrohexaazaisowurtzitane CL-20; the combustion agent is aluminum powder Al;
the curing agent is one or more of isophorone diisocyanate (IPDI), Toluene Diisocyanate (TDI), 1, 6-Hexamethylene Diisocyanate (HDI) or polyfunctional isocyanate (N-100).
Further, the curing catalyst is triphenyl bismuth TPB;
the anti-aging agent is one or more of N-methyl p-nitroaniline MNA or 2-nitrodiphenylamine 2-NDPA;
the bonding agent is tris (2-methyl aziridine) phosphine oxide MAPO, triethanolamine TEA or a neutral polymer bonding agent NPBA.
Example 1
The embodiment provides a liquid modified urea speed reducer BRS-1, and the preparation method comprises the following steps:
adding 2mol of chloropropionitrile and 2.4mol of triethylamine into 200ml of dichloromethane under the ice bath condition, uniformly mixing, and stirring for 30min at 0 ℃; then adding 1mol of urea into the system, and reacting for 12h at room temperature; adding a large amount of deionized water into the system to quench the reaction, extracting the product with dichloromethane, and vacuum drying for 12h to obtain BRS-1, wherein the infrared spectrum is shown in figure 1, and the structural formula is shown in formula (1).
CNCH2CH2HNCONHCH2CH2CN (1)。
Example 2
The embodiment provides a liquid modified urea speed reducer BRS-2, the preparation method is basically the same as that of the embodiment 1, and the raw material ratio is that urea: chloropropionitrile: pyridine is 1:4:4.8, an infrared spectrum is shown in figure 2, and a structural formula is shown in a formula (2).
(CNCH2CH2)2NCON(CH2CH2CN)2 (2)。
Examples 3 to 4, comparative examples 1 to 2
The preparation method of the embodiment 3 is that the solid propellant is obtained by adding the speed reducer BRS-1 obtained in the embodiment 1 into the HTPB propellant formula shown in the table 1, wherein the speed reducer accounts for 0.50% of the total mass of the solid propellant;
the preparation method of the embodiment 4 is that the solid propellant is obtained by adding the speed reducer BRS-2 obtained in the embodiment 2 into the HTPB propellant formula shown in the table 1, wherein the speed reducer accounts for 0.50% of the total mass of the solid propellant;
comparative example 1, i.e. prepared with the HTPB propellant formulation shown in table 1, gives a solid propellant;
the preparation method of comparative example 2 was to add urea, a conventional rate reducer, to the HTPB propellant formulation shown in table 1, to obtain a solid propellant, the rate reducer accounting for 0.50% of the total mass of the solid propellant;
TABLE 1 HTPB propellant formulation
Figure BDA0002841177880000071
The burning rate and pressure index test results of the solid propellant drug strip are shown in table 2.
TABLE 2 burning rate and pressure index of solid propellant with different retarders
Figure BDA0002841177880000072
Examples 5 to 6 and comparative examples 3 to 4
The preparation method of the embodiment 5 is that the solid propellant is obtained by adding the speed reducing agent BRS-1 obtained in the embodiment 1 into the GAP propellant formula shown in the table 3, wherein the speed reducing agent accounts for 0.50 percent of the total mass of the solid propellant;
the preparation method of the embodiment 6 is that the solid propellant is obtained by adding the speed reducing agent BRS-2 obtained in the embodiment 2 into the GAP propellant formula shown in the table 3, wherein the speed reducing agent accounts for 0.50 percent of the total mass of the solid propellant;
comparative example 3, prepared with the GAP propellant formulation shown in table 3, gave a solid propellant;
the preparation method of comparative example 4 was that, in the GAP propellant formulation shown in table 3, conventional rate-reducing agent urea was added to obtain a solid propellant, the rate-reducing agent accounting for 0.50% of the total mass of the solid propellant;
TABLE 3 GAP propellant formulations
Figure BDA0002841177880000081
The results of the burning rate and pressure index tests on the solid propellant sticks are shown in table 4.
TABLE 4 burning rate and pressure index of solid propellant with different retarders
Figure BDA0002841177880000082
Examples 7 to 8, comparative examples 5 to 6
The preparation method of the embodiment 7 comprises the steps of adding the speed reducer BRS-1 obtained in the embodiment 1 into a PET propellant formula shown in the table 5 to obtain a solid propellant, wherein the speed reducer accounts for 0.50% of the total mass of the solid propellant;
the preparation method of the embodiment 8 comprises the steps of adding the speed reducer BRS-2 obtained in the embodiment 2 into a PET propellant formula shown in the table 5 to obtain a solid propellant, wherein the speed reducer accounts for 0.50% of the total mass of the solid propellant;
comparative example 5, i.e. prepared by the PET propellant formulation shown in table 5, gives a solid propellant;
the preparation method of comparative example 6 was that, in the PET propellant formulation shown in table 5, conventional rate-reducing agent urea was added to obtain a solid propellant, the rate-reducing agent accounting for 0.50% of the total mass of the solid propellant;
TABLE 5 PET propellant formulations
Figure BDA0002841177880000091
The results of the burning rate and pressure index tests on the solid propellant sticks are shown in table 6.
TABLE 6 burning rate and pressure index of solid propellant with different retarders
Figure BDA0002841177880000092
Examples 9 to 10, comparative examples 7 to 8
The preparation method of the embodiment 9 is that the solid propellant is obtained by adding the speed reducer BRS-1 obtained in the embodiment 1 into the PEG propellant formula shown in the table 7, wherein the speed reducer accounts for 0.50 percent of the total mass of the solid propellant;
the preparation method of the example 10 is that the solid propellant is obtained by adding the speed reducer BRS-2 obtained in the example 2 into the PEG propellant formula shown in the table 7, wherein the speed reducer accounts for 0.50% of the total mass of the solid propellant;
comparative example 7, i.e., prepared by the PEG propellant formulation shown in table 7, yielded a solid propellant;
the preparation method of comparative example 8 was that, in the PEG propellant formulation shown in table 7, conventional rate-reducing agent urea was added to obtain a solid propellant, the rate-reducing agent accounting for 0.50% of the total mass of the solid propellant;
TABLE 7 PEG propellant formulations
Figure BDA0002841177880000101
The results of the mechanical property tests on the solid propellant billet are shown in table 8.
TABLE 8 burning rate and pressure index of solid propellant with different retarders
Figure BDA0002841177880000102
As can be seen from the above examples and comparative examples, the use effect of the liquid modified urea speed reducer is better than that of urea in the formula of HTPB, GAP, PET and PEG polyurethane propellants. The BRS-1 has the best use effect, the burning rate and the pressure index of the propellant can be reduced by 0.5 percent of the use amount, and the BRS-1 can be popularized and used as a speed reducer for a solid propellant.
The invention has been described in detail with reference to specific embodiments and illustrative examples, but the description is not intended to be construed in a limiting sense. Those skilled in the art will appreciate that various equivalent substitutions, modifications or improvements may be made to the technical solution of the present invention and its embodiments without departing from the spirit and scope of the present invention, which fall within the scope of the present invention. The scope of the invention is defined by the appended claims.
Those skilled in the art will appreciate that those matters not described in detail in the present specification are well known in the art.

Claims (9)

1. A liquid type modified urea speed reducer is characterized in that the structural formula of the liquid type speed reducer is as follows:
X2NCONX2；
in the structural formula, X is CnH2nCN or hydrogen, and the number of the hydrogen contained is less than or equal to 2; said C isnH2nIn CN, n is 1-10;
the liquid modified urea speed reducer is prepared by the following preparation method:
(1) dispersing nitrile halide and an acid-binding agent into dichloromethane under an ice bath condition, wherein the molar ratio of the nitrile halide to the acid-binding agent is 1: 1-1.5;
(2) adding urea into the solution obtained in the step (1), wherein the molar ratio of the urea to the nitrile halide is as follows: 1: 2-4.
(3) Adding deionized water to quench the reaction, extracting, and drying in vacuum to obtain a product;
the nitrile halide is a halogen element monosubstituent of acetonitrile, propionitrile, butyronitrile, valeronitrile, capronitrile, heptanonitrile, octanonitrile, nonanenitrile or decanonitrile, and the halogen element is chlorine, bromine or iodine;
the acid-binding agent is organic weak base.
2. The liquid-type modified urea speed reducer according to claim 1, wherein the molecular weight of the speed reducer is 150-1200.
3. The preparation method of the liquid-type modified urea speed reducer according to any one of claims 1 or 2, characterized by comprising the following steps:
(1) dispersing nitrile halide and an acid-binding agent into dichloromethane under an ice bath condition, wherein the molar ratio of the nitrile halide to the acid-binding agent is 1: 1-1.5;
(2) adding urea into the solution obtained in the step (1), wherein the molar ratio of the urea to the nitrile halide is as follows: 1: 2-4.
(3) Adding deionized water to quench the reaction, extracting, and drying in vacuum to obtain a product;
the nitrile halide is a halogen element monosubstituent of acetonitrile, propionitrile, butyronitrile, valeronitrile, capronitrile, heptanonitrile, octanonitrile, nonanenitrile or decanonitrile, and the halogen element is chlorine, bromine or iodine;
the acid-binding agent is organic weak base.
4. The method for preparing the liquid modified urea speed reducer according to claim 3, wherein in the step (2), the reaction temperature is room temperature, and the reaction time is not less than 12 h.
5. The method for preparing the liquid modified urea speed reducer according to claim 3, wherein the method comprises the following steps: the acid-binding agent is pyridine or triethylamine.
6. A solid propellant, comprising the liquid modified urea speed reducer of any one of claims 1 or 2, wherein the liquid modified urea speed reducer is 0.5-4% by mass.
7. The solid propellant is characterized by comprising the following components in percentage by mass:
Figure FDA0003452594240000021
Figure FDA0003452594240000031
the functional auxiliary agent comprises a curing catalyst, an anti-aging agent, a bonding agent and a speed reducing agent; the speed reducer is the liquid modified urea speed reducer of any one of claims 1 or 2, and the mass percent of the speed reducer is 0.5-4%.
8. The solid propellant according to claim 7, wherein the polyurethane binder is one or more of hydroxyl-terminated polybutadiene HTPB, polyaziridin glycidyl ether GAP, ethylene oxide-tetrahydrofuran copolyether PET, or polyethylene glycol PEG; the plasticizer is one or more of dioctyl sebacate DOS, nitroglycerin NG, butanetriol trinitrate BTTN, triethylene glycol dinitrate TEGDN or diethylene glycol dinitrate DEGDN; the oxidant is one or more of ammonium perchlorate AP or ammonium dinitramide ADN; the nitramine explosive is one or more of hexogen RDX, HMX or hexanitrohexaazaisowurtzitane CL-20; the combustion agent is aluminum powder Al; the curing agent is one or more of isophorone diisocyanate (IPDI), Toluene Diisocyanate (TDI), 1, 6-Hexamethylene Diisocyanate (HDI) or polyfunctional isocyanate (N-100).
9. The solid propellant of claim 7 wherein the curing catalyst is triphenylbismuth TPB; the anti-aging agent is one or more of N-methyl p-nitroaniline MNA or 2-nitrodiphenylamine 2-NDPA; the bonding agent is one or more of tris (2-methyl aziridine) phosphine oxide MAPO, triethanolamine TEA or neutral polymer bonding agent NPBA.
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