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Azido-terminated ethylene oxide-tetrahydrofuran block copolyether comprising carbamic acid ester structure unit and synthesis method of azido-terminated ethylene oxide-tetrahydrofuran block copolyether

A tetrahydrofuran block, hydroxyl-terminated ethylene oxide technology, used in polyether adhesives, adhesive types, adhesives, etc. It can solve the problems of agent energy level and poor mechanical strength, so as to ensure the low temperature mechanical properties, simple post-processing method and stable yield.

Active Publication Date: 2019-01-08
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the propellant based on the traditional polyurethane system has many disadvantages during use and storage: ① The isocyanate group is a relatively active group, which can also interact with CO in the air during the curing process with the hydroxyl group 2 , A small amount of moisture produces side reactions to generate bubbles, which affects the combustion performance, mechanical properties, processing costs and safety performance of the propellant; ②The curing system has poor compatibility with energetic oxidant molecules (such as AND, HNF, etc.) , thus limiting the overall energy level of the propellant
Finally, the tensile strength of the elastomer obtained from PUPE is 1.13MPa, the elongation at break is 320.2%, and the mechanical strength is not good

Method used

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  • Azido-terminated ethylene oxide-tetrahydrofuran block copolyether comprising carbamic acid ester structure unit and synthesis method of azido-terminated ethylene oxide-tetrahydrofuran block copolyether
  • Azido-terminated ethylene oxide-tetrahydrofuran block copolyether comprising carbamic acid ester structure unit and synthesis method of azido-terminated ethylene oxide-tetrahydrofuran block copolyether
  • Azido-terminated ethylene oxide-tetrahydrofuran block copolyether comprising carbamic acid ester structure unit and synthesis method of azido-terminated ethylene oxide-tetrahydrofuran block copolyether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The first step: Synthesis of chlorine-terminated oxirane-tetrahydrofuran block copolyether (ClTUTPE)

[0028] In a 250mL three-necked round-bottomed flask equipped with mechanical stirring, reflux condenser, and thermometer, sequentially add hydroxyl-terminated oxirane-tetrahydrofuran block copolyether (22.200g, 7.818mmol) and dibutyltin dilaurate (0.0138g , 0.022mmol), stir evenly. Then 2-chloroethyl isocyanate (1.741 g, 16.5 mmol) was added, and after stirring evenly, the temperature was slowly raised to 80° C., and the reaction was continued for 19 h. After the reaction, the unreacted 2-chloroethyl isocyanate was removed to obtain 23.8189 g of a colorless viscous liquid, which was chloro-terminated oxirane-tetrahydrofuran block copolyether, with a yield of 99.87%.

[0029] Structure Identification:

[0030] IR, ν max (cm -1 ): 3510, 3330(-NH-), 2940, 2860(-CH 2 -), 1724 (C=O), 1114 (-C-O-C-), 778 (C-Cl).

[0031] 1 H NMR (CDCl 3 , 500MHz): 5.47, 4.23, 3.63, 3...

Embodiment 2

[0041] The first step: Synthesis of chlorine-terminated oxirane-tetrahydrofuran block copolyether (ClTUTPE)

[0042] In a 250mL three-neck round-bottomed flask equipped with mechanical stirring, reflux condenser, and thermometer, sequentially add hydroxyl-terminated oxirane-tetrahydrofuran block copolyether (22.200g, 7.818mmol) and dibutyltin dilaurate (0.0095g , 0.015mmol), stir evenly. Then 2-chloroethyl isocyanate (2.146g, 20.338mmol) was added, after stirring evenly, the temperature was slowly raised to 70°C, and the reaction was continued for 22h. After the reaction, the unreacted 2-chloroethyl isocyanate was distilled off under reduced pressure to obtain 23.843 g of a colorless viscous liquid, chloro-terminated oxirane-tetrahydrofuran block copolyether, with a yield of 99.97%.

[0043] The second step: Synthesis of azido-terminated oxirane-tetrahydrofuran block copolyether (ATUTPE) In a 250mL three-necked round-bottomed flask equipped with mechanical stirring, reflux co...

Embodiment 3

[0045] The first step: Synthesis of chlorine-terminated oxirane-tetrahydrofuran block copolyether (ClTUTPE)

[0046] In a 250mL three-necked round-bottomed flask equipped with mechanical stirring, reflux condenser, and thermometer, sequentially add hydroxyl-terminated oxirane-tetrahydrofuran block copolyether (22.200g, 7.818mmol) and dibutyltin dilaurate (0.016g , 0.025mmol), stir evenly. Then 2-chloroethyl isocyanate (3.282g, 31.099mmol) was added, after stirring evenly, the temperature was slowly raised to 90°C, and the reaction was continued for 7h. After the reaction, the unreacted 2-chloroethyl isocyanate was distilled off under reduced pressure to obtain 23.810 g of a colorless viscous liquid, chloro-terminated oxirane-tetrahydrofuran block copolyether, with a yield of 99.83%.

[0047] The second step: Synthesis of azido-terminated oxirane-tetrahydrofuran block copolyether (ATUTPE)

[0048] In a 250mL three-necked round-bottomed flask equipped with mechanical stirring,...

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Abstract

The invention discloses an azido-terminated ethylene oxide-tetrahydrofuran block copolyether adhesive comprising a carbamic acid ester structure unit. A structural formula of the adhesive is shown bythe formula (I) as shown in the specification. A synthesis method of the azido-terminated ethylene oxide-tetrahydrofuran block copolyether adhesive comprises the following steps: taking a hydroxyl-terminated ethylene oxide-tetrahydrofuran block copolyether (HTPE) as a matrix, implementing a nucleophilic addition reaction with 2-chloroethyl isocyanate, and then implementing nucleophilic substitution with sodium azide to finally obtain the azido-terminated adhesive comprising the carbamic acid ester structure unit for curing in a Huisgen reaction. The synthesis method is simple, few in side effects and high in yield, and a curing method of the synthesized adhesive is wide in environmental suitability. The azido-terminated ethylene oxide-tetrahydrofuran block copolyether adhesive is mainly used for a composite solid propellant; in the formula, x is equal to an integer from 10 to 60; y is equal to an integer from 10 to 60; and m is a positive integer more than or equal to 1.

Description

technical field [0001] The invention relates to an azido-terminated oxirane-tetrahydrofuran block copolyether adhesive containing a carbamate structural unit and a synthesis method thereof. The compound can be used as an adhesive for a composite solid propellant and belongs to a solid propellant field. Background technique [0002] Hydroxyl-terminated oxirane-tetrahydrofuran block copolyether (HTPE) is a multi-block copolyether obtained by polymerization of tetrahydrofuran and ethylene oxide. The HTPE propellant based on the binder is a new type of insensitive propellant reported abroad, and it is a tactical missile for the purpose of improving the stunned ammunition properties of the HTPB composite propellant based on the hydroxyl-terminated polybutadiene (HTPB) binder. The solid propellant is currently an insensitivity propellant variety that has excellent mechanical properties and can fully meet the technical requirements of MIL-STD-2105C insensitivity. HTPE adhesives a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/325C08G65/333C09J171/02
CPCC08G65/325C08G65/33351C08G2650/04C09J171/02
Inventor 张倩莫洪昌卢先明刘宁徐明辉汪伟朱勇舒远杰王晓川
Owner XIAN MODERN CHEM RES INST