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Aliphatic diisocyanate and preparation method and purposes thereof

A diisocyanate and aliphatic technology, applied in the field of C21-36 aliphatic diisocyanate and its preparation, can solve the problems of harsh process conditions, easy occurrence of side reactions, and difficulty in industrialization, avoiding side reactions, being beneficial to industrial promotion and application, Less side effects

Active Publication Date: 2013-09-11
浙江优创材料科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The disadvantage of the phosgene method is that the process conditions are harsh, the toxicity is high, it is not easy to industrialize, the yield is low, the side reaction is easy to occur, and it brings inconvenience to the post-treatment, such as the reaction between the generated isocyanate and the raw material amine

Method used

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  • Aliphatic diisocyanate and preparation method and purposes thereof
  • Aliphatic diisocyanate and preparation method and purposes thereof
  • Aliphatic diisocyanate and preparation method and purposes thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: Preparation of C21 aliphatic diisocyanate

[0062] step 1:

[0063] Add 500g (1.7mol) methyl oleate, 123.5g (1.7mol) methyl acrylate and 1.5g hydroquinone to a 2000mL pressure reactor, replace the air in the kettle with nitrogen, heat up to 160-180°C, and react After 3.5 hours, the crude dibasic acid ester was obtained. The resulting product is a mixture of the following dibasic esters, and its structural formula is:

[0064]

[0065] Cool down and pump the reaction mixture into another 2 liter autoclave, then add 500g methanol and 30gPd (5%) / activated carbon catalyst (wet: 15g dry weight, 0.75gPd), vacuumize, nitrogen replacement, hydrogen replacement respectively. The reaction mixture was stirred at 160-170° C., 1.5-2.0 Mp for about 7.5 hours, until the hydrogen absorption was complete, and the stirring was stopped. The material was filtered off under nitrogen pressure, leaving the catalyst in the filter. With 500g methanol, the catalyst is backwa...

Embodiment 2

[0078] Example 2: C 22 Aliphatic diisocyanate

[0079] step 1:

[0080] Add 500g (1.7mol) methyl oleate, 171.7g (1.7mol) α-methyl methacrylate and 1.5g hydroquinone to a 2000mL pressure reactor, replace the air in the kettle with nitrogen, and heat up to 120~ 140°C, reacted for 3.5 hours to obtain crude dibasic acid. The resulting product is a mixture of the following dibasic esters, and its structural formula is:

[0081]

[0082] Cool down and pump the reaction mixture into another 2-liter autoclave, then add 500g ethanol and 30gPt (5%) / activated carbon catalyst (wet: dry weight 15g, 0.75gPd), vacuumize, nitrogen replacement, hydrogen replacement respectively. The reaction mixture was stirred at 150-180° C., 2.0-2.5 Mp for about 8 hours, until the hydrogen absorption was complete, and the stirring was stopped. The material was filtered off under nitrogen pressure, leaving the catalyst in the filter. With 500g of ethanol, the catalyst is backwashed into the reactor, a...

Embodiment 3

[0095] Example 3: C 22 Aliphatic diisocyanate

[0096] step 1:

[0097] Add 500g (1.7mol) methyl oleate, 171.7g (1.7mol) β-methyl methacrylate (methyl crotonate) and 1.5g hydroquinone to a 2000mL pressure reactor, and replace the air in the kettle with nitrogen , heated to 160-180°C, and reacted for 3.5 hours to obtain crude dibasic acid. The resulting product is a mixture of the following dibasic esters, and its structural formula is:

[0098]

[0099] Cool down and pump the reaction mixture into another 2 liter autoclave, then add 500g methanol and 30gPd (5%) / activated carbon catalyst (wet: 15g dry weight, 0.75gPd), vacuumize, nitrogen replacement, hydrogen replacement respectively. The reaction mixture was stirred at 160-170° C., 1.5-2.0 Mp for about 7.5 hours, until the hydrogen absorption was complete, and the stirring was stopped. The material was filtered off under nitrogen pressure, leaving the catalyst in the filter. With 500g methanol, the catalyst is backwas...

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Abstract

The invention provides a type of aliphatic diisocyanate with a novel chemical structure, which is C21-36 aliphatic diisocyanate, has the same excellent performance with other traditional aliphatic isocyanates, and is used for preparing polyurethane varnish, coating, elastomer, adhesive, textile finishing agent, rocket propellant and the like. The invention also provides a preparation method of this type of substance, which comprises the following steps that: (a) unsaturated dicarboxylic acid with a special structure or the ester solution thereof are catalyzed and hydrogenised to prepare saturated diacid; (b) the saturated diacid is dissolved into inert solvent and added with chloride agent to react and prepare binary acid chloride; (c) sodium azide is added in to react and prepare the corresponding azide; and (d) the azide is isomerized and decomposed to prepare an aliphatic diisocyanate crude product. The method is characterized by lower condition requirements, safety, environmental-friendliness, fewer side effects, high yield and easy wide popularization in industry.

Description

technical field [0001] The present invention relates to a class of aliphatic diisocyanate and its preparation method and application, especially to a class of C 21-36 Aliphatic diisocyanate and its preparation and use. Background technique [0002] Isocyanates are widely used in chemical fields such as coatings and adhesives, including aliphatic isocyanates and aromatic isocyanates. Among them, the materials generated by aliphatic isocyanate are stable and widely used. [0003] In the existing literature, it is mainly aimed at preparing the corresponding isocyanate or 2-heptyl-3,4-bis(9-isocyanate nonyl)-1-pentylcyclohexane (DDI1410) from low molecular weight fatty acids or amines. ) method. Generally, the phosgene method is used, and only low molecular weight aliphatic isocyanates are seen with the sodium azide method. [0004] The disadvantages of the phosgene method are harsh process conditions, high toxicity, difficult industrialization, low yield, prone to side reac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C265/14C07C263/12C09D175/04C08G18/75C09J175/04D06M15/564
Inventor 刘林学王研
Owner 浙江优创材料科技股份有限公司
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