CN116253870A - Terminal acrylate polyglycidyl ether nitrate, preparation method and application - Google Patents
Terminal acrylate polyglycidyl ether nitrate, preparation method and application Download PDFInfo
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- CN116253870A CN116253870A CN202211106056.6A CN202211106056A CN116253870A CN 116253870 A CN116253870 A CN 116253870A CN 202211106056 A CN202211106056 A CN 202211106056A CN 116253870 A CN116253870 A CN 116253870A
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- polyglycidyl ether
- acrylate
- ether nitrate
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229910002651 NO3 Inorganic materials 0.000 title claims abstract description 26
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 title claims abstract description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000000463 material Substances 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 14
- 238000001723 curing Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000002131 composite material Substances 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 238000000016 photochemical curing Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 abstract description 9
- 230000001070 adhesive effect Effects 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical class 0.000 abstract description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002360 explosive Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000010146 3D printing Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- JBLNCBDNFKLARF-UHFFFAOYSA-N 4,5-bis(ethenyl)-1h-imidazole Chemical compound C=CC=1N=CNC=1C=C JBLNCBDNFKLARF-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NDYLCHGXSQOGMS-UHFFFAOYSA-N CL-20 Chemical compound [O-][N+](=O)N1C2N([N+]([O-])=O)C3N([N+](=O)[O-])C2N([N+]([O-])=O)C2N([N+]([O-])=O)C3N([N+]([O-])=O)C21 NDYLCHGXSQOGMS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000003721 gunpowder Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- -1 methods Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- 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
- C06B23/001—Fillers, gelling and thickening agents (e.g. fibres), absorbents for nitroglycerine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses an acrylate-terminated polyglycidyl ether nitrate, a preparation method and application thereof. The structural formula of the disclosed compound is shown as (I); the terminal acrylate polyglycidyl ether nitrate (APGN) has terminal double bonds and can be rapidly cured under ultraviolet light; the terminal acrylate polyglycidyl ether nitrate (APGN) is an energy-containing adhesive, and compared with the energy-containing adhesive with halogen terminal double bonds in the prior art, the adhesive does not contain halogen elements, burns cleanly and has no corrosiveness.
Description
Technical Field
The invention relates to an energetic material, in particular to an acrylate-terminated polyglycidyl ether nitrate (APGN) compound, a preparation method and application thereof.
Background
At present, photo-curing 3D printing technology is widely focused by foreign researchers, and the adopted binder is epoxy resin, polyurethane resin, polyester resin and the like with end groups of acrylate groups, so that the polymer has the characteristic of being rapidly cured under ultraviolet light due to the double bonds of the end groups, but inert end group acrylic resin is used in the field of explosives and powders, and has adverse effect on energy promotion. Sagi Sevilia [ Sevilia S, yong M, grinsttein D, et al.Al.novel, printable energetic polymers [ J ]. Macromolecular Materials and Engineering,2019,1900018- & doi: 10.1002/name.201900018 ] reported an energetic mono/bis-vinylimidazole perchlorate (mono-and bisvinylimidazolium perchlorate) curable under ultraviolet light and useful for 3D printing. However, it is a perchlorate and the combustion gas contains chloride corrosion products.
The polyglycidyl ether nitrate (PGN) is an energy-containing adhesive with terminal hydroxyl groups, has the characteristics of high energy, high density, oxygen enrichment and the like, can be widely used in the fields of gunpowder, explosive and the like, wang Wei [ Wang Wei, han Shimin, zhang Deliang and the like, the synthesis and curing [ J ] of epoxy-terminated polyglycidyl ether nitrate, an energy-containing material, 2017,25 (1): 49-52 reports an epoxy-terminated polyglycidyl ether nitrate (e-PGN) cured with a curing agent which has a longer curing time at 60℃and a faster curing time of about 1 day when isophorone diamine is used as the curing agent.
Disclosure of Invention
Aiming at the defects and the shortcomings of the prior art, the invention provides an acrylate-terminated polyglycidyl ether nitrate.
The structural formula of the provided terminal acrylate polyglycidyl ether nitrate is shown as (I):
wherein n is 6-50.
The invention also provides a preparation method of the acrylic ester-terminated polyglycidyl ether nitrate. The specific synthetic route is as follows:
the corresponding preparation method comprises the following steps: at the temperature of 5 ℃ below zero to 5 ℃, dropwise adding an organic solvent solution of acrylic chloride into an organic solvent solution of PGN, and then carrying out reaction to prepare the acrylic ester-terminated polyglycidyl ether nitrate. Alternatively, the organic solvent solution of PGN is prepared by dissolving PGN in a mixed solution of dichloromethane and triethylamine. Optionally, the organic solvent solution of the acryloyl chloride is a dichloromethane solution of the acryloyl chloride or a chloroform solution of the acryloyl chloride.
The terminal acrylate polyglycidyl ether nitrate (APGN) has terminal double bonds and can be rapidly cured under ultraviolet light; the terminal acrylate polyglycidyl ether nitrate (APGN) is an energy-containing adhesive, and compared with the energy-containing adhesive with halogen terminal double bonds in the prior art, the adhesive does not contain halogen elements, burns cleanly and has no corrosiveness.
The terminal acrylate polyglycidyl ether nitrate can be used as an energetic material binder. In contrast to PGN and e-PGN, the compounds of the present invention are rapidly curable under ultraviolet light as binders for energetic materials without the need for heat curing. The compounds of the present invention are particularly useful in solid energetic materials such as RDX, HMX, HNIW, and the like.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of the compound prepared in example 1 of the present invention.
Detailed Description
Unless specifically stated otherwise, scientific and technical terms or methods herein have been understood or implemented according to the knowledge of one of ordinary skill in the relevant art. It should also be understood that the temperature, concentration referred to herein are approximations for purposes of illustration. Although methods and materials similar or equivalent to those described herein can be used in the practice of the present disclosure, some suitable methods and materials are described below. The materials, methods, solution concentrations, and examples described herein are illustrative only and are not intended to be limiting. In a specific scheme, a person skilled in the art can optimize the material proportion, concentration and operation parameter values involved in the method according to the disclosure of the invention by adopting a conventional experimental period so as to achieve the purpose of the invention.
The present invention will be described in further detail with reference to examples. The materials and equipment used in the examples below are all commercially available products.
Example 1:
adding 100g of PGN into a reactor provided with a mechanical stirring device, heating to 90 ℃, and decompressing to remove water for 1.5h; then cooled to room temperature, 500ml of dichloromethane and (3.730 g,36.9 mmol) of triethylamine were added;
then cooling to 0 ℃ with an ice salt bath, and dropwise adding 80ml of dichloromethane solution containing (2.47 g,27.3 mmol) of acryloyl chloride for 6h;
and after the dripping is finished, continuing to react for 24 hours, washing the reaction liquid to be neutral, separating the liquid, and decompressing and rectifying the oil phase to remove the solvent to obtain the product.
And (3) structural identification:
referring to FIG. 1, the nuclear magnetic spectrum of the prepared product: delta= 1.2,3.5 and 3.7ppm of characteristic absorption peaks ascribed to PGN, delta= 5.9,6.1 and 6.4ppm of proton characteristic peaks ascribed to terminal double bonds (-ch=ch2) in APGN, which demonstrates that APGN photosensitive energetic resins are acrylate modified PGN resins. In the nuclear magnetic carbon spectrum of APGN photosensitive energetic resins, δ=164.9 ppm is attributed to a proton characteristic peak on the ester bond (-c=o) in APGN terminal acrylate. Delta=132.5 ppm and 127.3ppm are proton characteristic peaks ascribed to double bonds in APGN end acrylate. Delta = 14.8, 26.3 and 68-72ppm are ascribed to proton characteristic peaks of PGN.
Infrared spectrum: 1128cm -1 The infrared characteristic absorption peak of PGN-C-O-, 3440cm -1 The infrared absorption peak of PGN terminal hydroxyl is 3440cm after modification of acrylate terminal group -1 The infrared absorption peaks at the PGN terminal hydroxyl groups disappeared, 1734 and 1190cm -1 There appears a distinct infrared characteristic absorption peak belonging to the-c=o bond in the acrylate and its absorbance is higher.
The above structural identification data confirm that the resulting material is indeed terminal acrylate polyglycidyl ether nitrate (APGN).
Properties of the prepared terminal acrylate polyglycidyl ether nitrate (APGN):
(1) Physical and chemical Properties
Appearance: a tan liquid;
solubility: insoluble in water; easily soluble in polar solvents such as ethanol, acetone, ethyl acetate, etc.;
density: 1.41g/cm 3 ；
Molecular weight: 1000;
curing time: curing for 30s under ultraviolet light;
(2) Energy performance
Example 2:
further mixing the compound prepared in the above example with an energetic material RDX in a mass ratio of 1:3, and photo-curing at room temperature and 40 ℃ to prepare two groups of composite energetic materials (experimental group 1 and experimental group 2);
and then the energy performance of the steel is detected according to the GJB770B-2005 method 703.1 closed burst test differential pressure method.
Meanwhile, a control group 1 and a control group 2 are arranged, corresponding detection is carried out, and the difference between each control group and the experimental group is shown in the table 1:
TABLE 1
The energy of each of the experimental group 1 and the experimental group 2 is 1286J/g, and the curing time is 60s (room temperature 25 ℃) and 30s (40 ℃) respectively through the test and detection of the powder strength;
in comparison with the control group 1, the energy of the composite energetic material adopting APGN as the adhesive is slightly higher than that of the composite energetic material adopting e-PGN as the adhesive, but the curing time is shortened from 1 day to 30-60 s, and the curing time is greatly shortened;
in comparison with control group 2, the energy of the composite energetic material using APGN as the binder is significantly higher than that of the composite energetic material using inert urethane acrylate as the binder, and the curing time is comparable.
Therefore, the acrylate-terminated polyglycidyl ether nitrate (APGN) has the characteristics of quick solidification under ultraviolet light, large heat generation, no halogen and the like, and can be applied to the fields of quick preparation of high-energy propellant, low-signal propellant, explosive and the like.
Claims (8)
1. The structural formula of the terminal acrylate polyglycidyl ether nitrate is shown as (I):
wherein n is 6-50.
2. The method for preparing the acrylate-terminated polyglycidyl ether nitrate according to claim 1, characterized in that the method comprises the following steps: at the temperature of 5 ℃ below zero to 5 ℃, dropwise adding an organic solvent solution of acrylic chloride into an organic solvent solution of PGN, and then carrying out reaction to prepare the acrylic ester-terminated polyglycidyl ether nitrate.
3. The method for preparing the terminal acrylate polyglycidyl ether nitrate according to claim 2, wherein the organic solvent solution of PGN is prepared by dissolving PGN in a mixed solution of dichloromethane and triethylamine.
4. A method of preparing the acrylate-terminated polyglycidyl ether nitrate according to claim 3, wherein the organic solvent solution of the acryl chloride is a methylene chloride solution of the acryl chloride or a chloroform solution of the acryl chloride.
5. Use of the terminal acrylate-based polyglycidyl ether nitrate according to claim 1 as an energetic material binder.
6. A composite energetic material comprising an energetic material and a binder, wherein the binder is the terminal acrylate-based polyglycidyl ether nitrate according to claim 1.
7. The composite energetic material of claim 1, wherein the composite energetic material is prepared by photocuring.
8. The composite energetic material of claim 1, wherein the composite energetic material is prepared by ultraviolet light curing.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140078552A (en) * | 2012-12-17 | 2014-06-25 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | bis ether compounds having fluorene backbone and resin composition |
| CN110172142A (en) * | 2019-06-26 | 2019-08-27 | 西安近代化学研究所 | Acrylate-based client glycidol ether nitrate-tetrahydrofuran copolyether prepolymer |
| CN110183645A (en) * | 2019-06-26 | 2019-08-30 | 西安近代化学研究所 | A kind of light-cured type nitrate ester polyether and its synthetic method |
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- 2022-09-09 CN CN202211106056.6A patent/CN116253870A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140078552A (en) * | 2012-12-17 | 2014-06-25 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | bis ether compounds having fluorene backbone and resin composition |
| CN110172142A (en) * | 2019-06-26 | 2019-08-27 | 西安近代化学研究所 | Acrylate-based client glycidol ether nitrate-tetrahydrofuran copolyether prepolymer |
| CN110183645A (en) * | 2019-06-26 | 2019-08-30 | 西安近代化学研究所 | A kind of light-cured type nitrate ester polyether and its synthetic method |
Non-Patent Citations (3)
| Title |
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| 余柳俭: ""水溶性光固化体系及其对有机磷水解酶的固定化研究"", 《中国优秀硕士学位论文全文数据库 基础科学辑》, 15 February 2019 (2019-02-15), pages 16 * |
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