Preparation method for side-chain azo-type aqueous polyurethane

A water-based polyurethane and azo technology, which is applied in the field of side-chain azo-type water-based polyurethane and its preparation, can solve the problems of large amount of solvent used, low solid content of materials, water resistance of products, and problems with thermodynamic properties, and achieve uniform distribution , not easy to migrate, and the effect of maintaining the azo functional properties for a long time

Active Publication Date: 2014-03-19
宏元(江门)化工科技有限公司 +1
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

The method steps are loaded down with trivial details, and yield is low, and the amount of solvent used is large
[0005] Preparation and characterization of multi-responsive polyurethane nanoparticles containing azo chromophores reported in "Chinese Science and Technology Papers" (December 2012, Volume 7, Issue 12, Pages 945-948), using polyethylene oxide as the soft segment, Diisocyanate is used as a hard segment, polymerized with azodiol to obtain a polymer, an...

Method used

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  • Preparation method for side-chain azo-type aqueous polyurethane
  • Preparation method for side-chain azo-type aqueous polyurethane
  • Preparation method for side-chain azo-type aqueous polyurethane

Examples

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Effect test

Embodiment 1

[0036] Add 15.35 grams of 4-ethylaniline into 100 mL of water, then slowly add 45 grams of concentrated sulfuric acid with a concentration of 98% by mass, stir magnetically for 5 minutes, cool down to 0-5°C, and then drop it within 1 minute from 8.75 A solution formed of 1 g of sodium nitrite and 15 mL of water was kept at 0-5°C for 1 hour to obtain a diazonium salt solution of 4-ethylaniline.

[0037] Add 5 g of acetic acid, 24 mL of methanol and 25 mL of water into 23.45 g of N,N-dihydroxyethylaniline, keep the reaction system at 0-5°C after forming a solution, and add the previously prepared 4-ethylaniline dropwise under magnetic stirring The diazonium salt solution, and the pH value of the system is adjusted to 6 by adding a substance concentration of 1M sodium hydroxide solution. Keep the reaction at 0-5°C for 2 hours, then filter, and recrystallize the obtained precipitate with a mixture of ethanol and water with a volume ratio of 2.5:1 to obtain azodiol N,N-dihydroxyeth...

Embodiment 2

[0042] Add 9 grams of aniline to 60 mL of water, then slowly add 29.4 grams of concentrated hydrochloric acid with a concentration of 37% by mass, dissolve and cool down to 0-5 °C. Under stirring, add a solution of 6.66 g of sodium nitrite and 10.5 mL of water dropwise within 1 minute, and keep at 0-5° C. for 1 hour to obtain a diazonium salt solution of aniline.

[0043] Add 30mL of methanol and 18mL of acetic acid into 15mL of water, then add 17.4g of N,N-dihydroxyethylaniline under stirring, cool down to 0-5°C after forming a solution, and add dropwise the diazonium salt solution of aniline prepared above , and the pH value of the system is adjusted to 6 by adding a substance whose concentration is 1M sodium hydroxide solution. Keep the system at 0-5°C for 2 hours, filter, wash the precipitate with water once, and then recrystallize the precipitate with a mixture of ethanol and water at a volume ratio of 2.5:1 to obtain azodiol N,N-dihydroxy Ethyl-4-phenylazoaniline (AZOb)...

Embodiment 3

[0050] Add 1.5g of butyl p-aminobenzoate and 3mL of acetic acid into 7.5mL of water, then slowly add 1.27g of concentrated hydrochloric acid with a concentration of 37% by mass, and cool down to 0-5°C after forming a solution; within 1 minute under stirring After the solution prepared by 0.53 g of sodium nitrite and 1.1 g of water was added dropwise, the reaction was maintained at 0-5° C. for 1 hour to obtain a diazonium salt solution of butyl p-aminobenzoate.

[0051] Add 1.44 g of N,N-dihydroxyethylaniline to 5 mL of methanol and 1 mL of acetic acid, stir to form a solution, then cool down to 0-5 °C, add the diazonium salt solution of butyl p-aminobenzoate prepared above dropwise , and the pH value of the system is adjusted to 6 by adding a substance whose concentration is 1M sodium hydroxide solution. Keep the system at 0-5°C for 2 hours, adjust the pH of the system to 7, filter the product, wash with water, and then recrystallize the product with ethanol to obtain azodiol ...

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Abstract

A preparation method for side-chain azo-type aqueous polyurethane is characterized in that a dihydric alcohol containing an azo chromophore and with a symmetric structure is taken as a reactant, and is reacted with a macro-molecule dihydric alcohol and a hydrophilic chain extender for synthesizing cation side-chain azo-type aqueous polyurethane and anion side-chain azo-type aqueous polyurethane. Due to the fact that azo dihydric alcohol is one of the chain extenders, the azo chromophore is in the side chain of the polyurethane molecular chain and other micromolecule chain extenders can be partially or completely replaced, the azo chromophore functional structure has controllable content in the polyurethane molecular chain; the azo chromophore is distributed uniformly and not easy to transfer, and the azo function characteristic can be retained durably; the reversible cis-trans isomerism configuration variation can be generated under the excitation of relatively low energy; and by adjusting the use amount of azo dihydric alcohol, the structure of the polyurethane molecular chain hard segment can be controlled, the side-chain azo-type aqueous polyurethane obtains the azo function characteristics, and also the optical performances, the thermodynamic performances, some functional characteristics and the like of aqueous polyurethane are adjusted.

Description

technical field [0001] The invention belongs to the technical field of water-based polyurethane materials, in particular to side-chain azo-type water-based polyurethane based on azo chromophores in azodiols and a preparation method thereof. Background technique [0002] The United States "Macromolecules" (Macromolecules, 1972, Volume 5, pages 171-177) reported the photoisomerization effect of side chain and main chain azobenzene bulk polymers. As an important class of optical information functional materials, azo polymer materials have become one of the hotspots of people's attention in recent years. The unique azo chromophore structure in the molecular chain of azo polymer materials, including polyurethane, makes it have reversible cis-trans configuration isomerism characteristics under light excitation, and is used in organic optical information storage, grating, optical Materials fields such as switches and light sensing devices have important application value. Because...

Claims

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Application Information

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IPC IPC(8): C08G18/66C08G18/32
CPCC08G18/0814C08G18/0823C08G18/10C08G18/4238C08G18/4825C08G18/4854C08G18/73C08G18/755C08G18/3836C08G18/3275C08G18/348C08G18/3206
Inventor 李发萍张兴元李军配郑燕
Owner 宏元(江门)化工科技有限公司
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