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Synthesis method of alkynyl-terminated polybutadiene containing carbamate element

A technology of alkyne-terminated polybutadiene and hydroxyl-terminated polybutadiene, which is applied in the field of polymer materials, can solve the problems of poor mechanical properties and affect the mechanical properties of polytriazole elastomers, and achieve the effect of excellent mechanical properties

Active Publication Date: 2017-02-15
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the first step reaction generates more chain extension products of toluene-2,4-diisocyanate to hydroxyl-terminated polybutadiene, which seriously affects the mechanical properties of the prepared polytriazole elastomer, and the tensile strength is 1.52Mpa , poor mechanical properties

Method used

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  • Synthesis method of alkynyl-terminated polybutadiene containing carbamate element
  • Synthesis method of alkynyl-terminated polybutadiene containing carbamate element
  • Synthesis method of alkynyl-terminated polybutadiene containing carbamate element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1) Preparation of propargyl (3-isocyanato-4-methyl)phenylcarbamate

[0018] Under nitrogen protection, 5.6 g (0.1 mol) propargyl alcohol was added dropwise to a mixture of 52.2 g (0.3 mol) toluene-2,4-diisocyanate and 100 mL of toluene, and the temperature was maintained at 40°C during the dropwise addition. After the completion of the dropwise addition, the reaction was completed at 60°C for 6 hours. After cooling down, a solid was precipitated, which was filtered and dried to obtain 14 g of a white solid with a yield of 60.9%.

[0019] Characterization data:

[0020] 1 H NMR (DMSO-d 6 , 500MHz): δ=9.90(s, 1H), 7.31(s, 1H), 7.19(m, 2H), 4.76(d, 2H, J=2.0Hz), 3.56(t, 1H, J=2.0Hz) ,2.23(s,3H); 13 C NMR (DMSO-d 6 , 125MHz): δ=153.0, 138.2, 132.3, 131.3, 127.2, 124.6, 116.4, 114.9, 79.3, 78.0, 52.5, 17.6.

[0021] IR(KBr,cm -1 ): ν=3331, 3294, 2281, 2124, 1714, 1623, 1553, 1516, 1388, 1314, 1283, 1227, 1075, 916;

[0022] Elemental Analysis: C 12 H 10 N 2 O 3...

Embodiment 2

[0031] (1) Preparation of propargyl (3-isocyanato-4-methyl)phenylcarbamate

[0032] Under nitrogen protection, 5.6 g (0.1 mol) propargyl alcohol was added dropwise to a mixture of 69.6 g (0.4 mol) toluene-2,4-diisocyanate and 100 mL toluene, and the temperature was maintained at 50°C during the dropwise addition. After the completion of the dropwise addition, the reaction was completed at 60°C for 6 hours. After cooling, a solid was precipitated, which was filtered and dried to obtain 14.2 g of a white solid with a yield of 62.0%.

[0033] (2) Synthesis of alkynyl-terminated polybutadiene containing carbamate units

[0034] Under nitrogen protection, 9.4g (40.9mmol) propargyl (3-isocyanato-4-methyl)phenylcarbamate, 60g hydroxyl terminated polybutadiene (40.9mmol OH) and 250mL dry toluene were added to the reaction bottle. After stirring at 70° C. for 24 hours, the reaction was terminated, and the toluene was removed by concentration to obtain 68.0 g of a pale yellow solid w...

Embodiment 3

[0036] (1) Preparation of propargyl (3-isocyanato-4-methyl)phenylcarbamate

[0037] Under nitrogen protection, 5.6 g of propynol (0.1 mol) was added dropwise to a mixture of 87 g (0.5 mol) of toluene-2,4-diisocyanate and 100 mL of toluene, and the temperature was maintained at 50°C during the dropwise addition. After completion of the dropwise addition, the reaction was completed at 70°C for 5 hours. After cooling, a solid was precipitated, which was filtered and dried to obtain 15.6 g of a white solid with a yield of 68.1%.

[0038] (2) Synthesis of alkynyl-terminated polybutadiene containing carbamate units

[0039] Under nitrogen protection, 9.4g (40.9mmol) propargyl (3-isocyanato-4-methyl)phenylcarbamate, 60g hydroxyl terminated polybutadiene (40.9mmol OH) and 250mL dry toluene were added to the reaction bottle. The reaction was terminated after stirring at 60° C. for 24 hours, and 67.0 g of light yellow solid was obtained by concentrating to remove toluene, and the yie...

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Abstract

The invention discloses a synthesis method of alkynyl-terminated polybutadiene containing a carbamate element. The structural formula of alkynyl-terminated polybutadiene is shown in formula I. The synthesis process of alkynyl-terminated polybutadiene comprises steps as follows: (1) propynol and excessive toluene-2,4-diisocyanate react to produce propargyl(3-isocyanate-4-methyl)phenyl carbamate; (2) propargyl(3-isocyanate-4-methyl)phenyl carbamate and hydroxyl-terminated polybutadiene are subjected to an addition reaction to produce alkynyl-terminated polybutadiene containing the carbamate element. The synthesized alkynyl-terminated polybutadiene containing the carbamate element adopts a specific chain structure, has no side reaction and enables polytriazole elastomers to have excellent mechanical performance when applied to the polytriazole elastomers.

Description

technical field [0001] The invention relates to a method for synthesizing alkynyl-terminated polybutadiene containing carbamate units. The compound can be used as a binder for composite solid propellants, and belongs to the technical field of polymer materials. [0002] technical background [0003] Binder is an important component of solid propellant. It acts as skeleton and matrix to bond oxidant, metal aluminum powder, plasticizer and other additive components together, so that propellant formula has certain geometric shape and mechanical properties. Hydroxy-terminated polybutadiene (HTPB) propellants and hydroxyl-terminated polyether (HTPE) propellants, which are currently widely used in weapons and equipment, are both cured and reacted with hydroxyl-terminated prepolymers and isocyanates at a certain temperature to form polyurethane elastomers. The reaction system is sensitive to moisture. The moisture in the environment and in the raw materials causes a series of side r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F8/30C08F136/06C08G18/71C08G18/69
CPCC08F8/30C08G18/69C08G18/714C08F136/06
Inventor 李辉赵凤起王伯周廉鹏李祥志
Owner XIAN MODERN CHEM RES INST
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