Azo-like liquid crystal monomer with reaction character and preparation method thereof

A liquid crystal monomer and azo technology, applied in the field of azo liquid crystal monomer and its preparation, can solve the problems of low reactivity and the like, and achieve the effects of easy raw materials, reasonable product cost, simple and safe operation

Inactive Publication Date: 2008-06-04
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to overcome the low reactivity existing in the prior art and the disadvantages of not being easy to initiate graft polymerization reactions, the present invention proposes a kind of azo liquid crystal monomer with reactive characteristics and its synthesis method

Method used

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  • Azo-like liquid crystal monomer with reaction character and preparation method thereof
  • Azo-like liquid crystal monomer with reaction character and preparation method thereof
  • Azo-like liquid crystal monomer with reaction character and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The structural formula of the azo-based liquid crystal monomer with reactive properties in this embodiment is:

[0017]

[0018] where: n 1 =7,n 2 = 1, n 3 =2, alkenyloxy ortho-substituted.

[0019] The synthetic method of 2-allyloxy-4-octyloxy-(p-propylbiphenylazo)benzene:

[0020] (1) 2-allyloxy-4-octyloxybenzamide: mix 10g of 2-allyloxy-4-octyloxybenzoic acid with 2.3g of urea, pass dry nitrogen, add 50ml of toluene and heat to reflux During this process, the water was separated through the water separator. After 15 hours of reaction, the water pump was evacuated, the solvent was evaporated under reduced pressure, and 37ml of toluene was recovered. The residual liquid was poured into n-propanol, stirred to produce precipitation, and filtered to obtain the crude product. Recrystallized with ethanol to obtain 6.7 g light yellow solid powder, yield 67.1%.

[0021] (2) 2-allyloxy-4-octyloxyaniline: In a low-temperature bath with temperature controlled at -10°C, s...

Embodiment 2

[0024] The structural formula of the azo-based liquid crystal monomer with reactive properties in this embodiment is:

[0025]

[0026] where: n 1 =5,n 2 = 3, n 3 =3, alkenyloxy ortho-substituted.

[0027] The synthetic method of 2-enyloxy-4-hexyloxy-(p-butylbiphenylazo)benzene is:

[0028] (1) 2-(4'-pentenyloxy)-4-hexyloxybenzamide: mix 10g of 2-(4'-pentenyloxy)-4-hexyloxybenzoic acid with 2.3g of urea , pass through dry nitrogen, add 50ml of toluene and heat to reflux. During this process, the water is separated through the water separator. After 15 hours of reaction, the water pump is vacuumed, the solvent is evaporated under reduced pressure, and 37ml of toluene is recovered, and the residual liquid is poured into n-propanol , stirred to produce a precipitate, filtered to obtain a crude product, and recrystallized with ethanol to obtain 6.77g of a light yellow solid powder with a yield of 67.9%.

[0029] (2) 2-(4'-pentenyloxy)-4-hexyloxyaniline: Control the tempera...

Embodiment 3

[0032] The structural formula of the azo-based liquid crystal monomer with reactive properties in this embodiment is:

[0033]

[0034] where: n 1 =7,n 2 = 3, n 3 =2, alkenyloxy meta-substituted.

[0035] The synthetic method of 3-(4'-pentenyloxy)-4-octyloxy-(p-propylbiphenylazo)benzene is:

[0036] (1) 3-(4'-pentenyloxy)-4-octyloxybenzamide: mix 10g of 3-(4'-pentenyloxy)-4-octyloxybenzoic acid with 2.1g of urea , pass through dry nitrogen, add 50ml of toluene and heat to reflux. During this process, the water is separated through the water separator. After 15 hours of reaction, the water pump is vacuumed, the solvent is evaporated under reduced pressure, and 37ml of toluene is recovered, and the residual liquid is poured into n-propanol , stirred to produce a precipitate, filtered to obtain a crude product, and recrystallized with ethanol to obtain 6.67 g of light yellow solid powder, with a yield of 66.9%.

[0037] (2) 3-(4'-pentenyloxy)-4-octyloxyaniline: In a low-tem...

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Abstract

The invention discloses an azo liquid crystal monomer with reaction properties and a preparation method thereof. The structural formula of the compound is listed, wherein, the n1 is an integer between 6 and 14, n2 is an integer between 1 and 7 and n3 is an integer between 1 and 5; the substitute position of the dilute oxygen is the adjacent position or contraposition of alkoxy; a synthesis method of the compound is that: the substituted dilute oxygen pairs by alkoxy benzoic acid is adopted as raw material to obtain aniline compounds by processes of amidation and hoffman degradation reaction; then low temperature diazotization coupling is carried out to obtain the new liquid crystal compound. A central bridge bond of the liquid crystal monomer of the invention is the azo group and has optical activity and a side chain of the invention is double bonds with reactivity; at last, novel waist connected type macromolecule liquid crystal and liquid crystal elastomer are made by polymerization or graft the double bonds to macromolecule main chain. The invention has easy obtained raw material, simple and safe operation and being applied to such fields as non-linear optical materials, optical information storage, optical switch, display, artificial muscles, shape memory and biomedicine.

Description

(1) Technical field [0001] The invention relates to an azo liquid crystal compound in the field of chemistry, in particular to an azo liquid crystal monomer with reactive properties and a preparation method thereof. (2) Background technology [0002] Liquid crystals have both the fluidity of liquids and the anisotropic characteristics of crystals. Using their anisotropic characteristics under the action of light, electricity, magnetism and heat, liquid crystals are widely used in display, information, biomedicine and smart materials superior. In 1950, A. Elliot introduced liquid crystal properties into polymer materials, obtained a new liquid crystal polymer material, and broadened the application range of liquid crystals. In 1981, H. Finkelmann first synthesized liquid crystal elastomers. He combined the alignment order of liquid crystals with the entropy elasticity of polymer networks to obtain this new type of polymer with excellent performance that can be used in smart ...

Claims

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Application Information

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IPC IPC(8): C09K19/24
Inventor 朱光明邓登宋斐
Owner NORTHWESTERN POLYTECHNICAL UNIV
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