CN108822550B - Preparation method of novel liquid crystal elastomer material - Google Patents
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Abstract
The invention relates to the field of new material preparation, in particular to a preparation method of a new liquid crystal elastomer material; according to the invention, polyaniline conjugated polymer powder is added into a liquid crystal system to prepare a new liquid crystal elastomer material; the novel liquid crystal elastomer material prepared by the scheme has good stability, better mechanical strength, quick response to near infrared light and obvious photo-thermal effect, and is an ideal shape memory liquid crystal elastomer material.
Description
Technical Field
The invention relates to the field of material preparation, in particular to a preparation method of a novel liquid crystal elastomer material.
Background
Different from soft substances such as common colloid, polymer and the like, the liquid crystal elastomer is an anisotropic force-sequence coupling soft substance which is sensitive to multiple fields and has elasticity and liquid crystal property at the same time. Therefore, the rubber elastomer material is different from the prior rubber elastomer material, has novel characteristics and has wide application prospects in various fields.
CN106883863A discloses a liquid crystal elastomer driving element, comprising a liquid crystal elastomer capable of reversible deformation around the liquid crystal transition temperature, the liquid crystal elastomer having a cross-linked network comprising interconnected liquid crystal molecules, molecules containing allyl sulfide groups, flexible chains and cross-linking agents. The invention also relates to a preparation method of the liquid crystal elastomer driving element, which comprises the following steps: adding liquid crystal molecules, molecules containing allyl sulfide groups, flexible chains and a cross-linking agent into a solvent to form a mixture solution; polymerizing the mixture solution to polymerize liquid crystal molecules, molecules containing allyl sulfide groups, flexible chains and a crosslinking agent into a crosslinked network to form a liquid crystal elastomer; and carrying out orientation treatment on the liquid crystal elastic body to obtain the liquid crystal elastic body driving element. The invention also relates to the application of the liquid crystal elastomer as a driving element applied to artificial muscles, blind displays, sensors, microfluidic system valves or intelligent response interface materials.
CN106103653A provides a method of producing Liquid Crystal Elastomer (LCE) based components. The method comprises the following steps: (i) providing or producing micron-sized or nano-sized LCE particles, (ii) dispersing said particles in an uncured liquid polymer, (iii) orienting the nematic director of said particles, and (iv) shaping and curing said matrix/particle mixture. The composite material formed by this method is a Polymer Dispersed Liquid Crystal Elastomer (PDLCE) with tailored properties that can be shaped into any form.
CN101113200A provides a preparation method of a main chain type liquid crystal elastomer, which comprises the steps of carrying out hydrosilylation reaction on diene monomers containing mesogens, hydrogen-containing polysiloxane and a silane coupling agent under the action of a catalyst to obtain a prepolymer, then bonding the prepolymer into a network structure containing the mesogens and low crosslinking density by utilizing the hydrolysis of siloxane, and obtaining the liquid crystal elastomer through proper stretching. The method has the characteristics of simple operation, difficult gelation, easy control of the crosslinking density of the elastomer and the like.
Near-infrared response liquid crystal elastomers have become a new research hotspot due to the wide application prospect in the biological field. However, the near-infrared response liquid crystal elastomer prepared by the prior art has the defects of low photo-thermal conversion efficiency, poor mechanical property and low response speed, and further application of the near-infrared response liquid crystal elastomer is limited.
Disclosure of Invention
In order to solve the problems, the invention provides a preparation method of a novel liquid crystal elastomer material.
A preparation method of a new liquid crystal elastomer material adopts the following preparation technical scheme:
according to the mass portion, 124-136 portions of p-methoxybenzoic acid-4-allyloxy biphenyl monophenol ester, 18-26 portions of chiral cross-linking agent, 31-36 portions of polymethyl hydrogen-containing siloxane, 0.01-0.1 portion of 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ], 0.01-0.1 portion of 9, 9-diethyl fluorene-2-boric acid, 0.05-0.5 portion of 6-amino-2, 3-dihydroindene-1-one, 0.05-0.5 portion of tris [ N, N-bis (trimethylsilane) amine ] erbium, 0.8-1.6 portions of polyaniline powder and 200-300 portions of toluene are added into a reaction kettle and stirred for 30-60min to be dissolved; dissolving 0.05-0.15 part of catalyst by 2.5-3.5 parts of toluene, adding into a reaction kettle, controlling the temperature at 40-60 ℃, reacting for 30-60min, adding the material into a mold, ultrasonically treating for 10-20min to eliminate bubbles, and placing the mold into a drying oven at 60-80 ℃ to crosslink for 2-6h to form a film; after the film-formed elastomer is unidirectionally stretched by 50-70 percent, the film-formed elastomer is continuously placed into a drying oven at the temperature of 60-80 ℃ for crosslinking for 36-48h, and the novel liquid crystal elastomer material can be obtained.
The catalyst is dichloro (1, 5-cyclooctadiene) platinum or 1, 5-cyclooctadiene palladium dichloride or (1, 5-cyclooctadiene) platinum dichloride.
The chiral cross-linking agent is prepared according to the following scheme:
adding 120 parts by mass of 100-one tetrahydrofuran, 18-26 parts by mass of triethylamine and 25-35 parts by mass of chiral diphenol into a reaction kettle, and stirring for 30-40min at room temperature to dissolve uniformly; then adding 80-100 parts of diluted acyl chloride to dissolve in 200-300 parts of tetrahydrofuran, slowly adding into a reaction kettle, heating and controlling the temperature to 60-80 ℃, and reacting for 18-36 h; after the reaction is finished, pouring the system into 800 portions of 600-800 portions of water for precipitation, then filtering, washing with water to be neutral, and drying to obtain the chiral cross-linking agent.
The dilute acyl chloride is 8-methyl-6-nonenoyl chloride, undecenoyl chloride or 5-norbornene-2-acyl chloride.
The chiral diphenol is isosorbide or (R) -spirocyclic diphenol or chiral 1, 1-binaphthyl-2, 2-diphenol.
The novel liquid crystal elastomer material prepared by the scheme has good stability, better mechanical strength, quick response to near infrared light and obvious photo-thermal effect, and is an ideal shape memory liquid crystal elastomer material.
Detailed Description
The invention is further illustrated by the following specific examples:
example 1
A preparation method of a new liquid crystal elastomer material adopts the following preparation technical scheme:
adding 130 parts by mass of p-methoxybenzoic acid-4-allyloxy biphenyl monophenol ester, 22 parts by mass of chiral cross-linking agent, 33 parts by mass of polymethyl hydrogen-containing siloxane, 0.03 part by mass of 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ], 0.05 part by mass of 9, 9-diethylfluorene-2-boric acid, 0.1 part by mass of 6-amino-2, 3-dihydroindene-1-one, 0.3 part by mass of tris [ N, N-bis (trimethylsilane) amine ] erbium, 1.2 parts by mass of polyaniline powder and 250 parts by mass of toluene into a reaction kettle, and stirring for 350min to dissolve; then dissolving 0.1 part of catalyst by using 3 parts of toluene, adding the solution into a reaction kettle, controlling the temperature at 50 ℃, reacting for 50min, then adding the material into a mold, ultrasonically treating for 15min to eliminate bubbles, and placing the mold into a 70 ℃ oven to crosslink for 4h to form a film; after the film-formed elastomer is stretched in a unidirectional mode by 60%, the elastomer is continuously placed into a drying oven at the temperature of 70 ℃ for crosslinking for 42 hours, and then a new liquid crystal elastomer material is obtained.
The catalyst is (1, 5-cyclooctadiene) platinum dichloride.
The chiral cross-linking agent is prepared according to the following scheme:
adding 110 parts of tetrahydrofuran, 22 parts of triethylamine and 30 parts of chiral diphenol in parts by mass into a reaction kettle, and stirring for 35min at room temperature to dissolve uniformly; then, dissolving 90 parts of diluted acyl chloride in 250 parts of tetrahydrofuran, slowly adding the mixture into a reaction kettle, heating to control the temperature to 70 ℃, and reacting for 25 hours; after the reaction is finished, pouring the system into 700 parts of water for precipitation, then filtering, washing with water to be neutral, and drying to obtain the chiral cross-linking agent.
The dilute acyl chloride is 5-norbornene-2-acyl chloride.
The chiral diphenol is 1, 1-binaphthyl-2, 2-diphenol.
The 50mg elastomer shrinkage set force of the test sample produced is 14.9X 10-3N, glass transition temperature 64.1 ℃.
Example 2
A preparation method of a new liquid crystal elastomer material adopts the following preparation technical scheme:
adding 124 parts by mass of p-methoxybenzoic acid-4-allyloxy biphenyl monophenol ester, 18 parts by mass of chiral cross-linking agent, 31 parts by mass of polymethylhydrosiloxane, 0.01 part by mass of 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ], 0.01 part by mass of 9, 9-diethylfluorene-2-boric acid, 0.05 part by mass of 6-amino-2, 3-dihydroindene-1-one, 0.05 part by mass of tris [ N, N-bis (trimethylsilane) amine ] erbium, 0.8 part by mass of polyaniline powder and 200 parts by mass of toluene into a reaction kettle, and stirring for 30min to dissolve; then dissolving 0.05 part of catalyst by 2.5 parts of toluene, adding the solution into a reaction kettle, controlling the temperature at 40 ℃, reacting for 30-60min, adding the material into a mold, ultrasonically treating for 10min to eliminate bubbles, and placing the mold into a 60 ℃ oven to crosslink for 2-6h to form a film; after the film-formed elastomer is stretched unidirectionally by 50 percent, the elastomer is continuously placed into a drying oven at 60 ℃ for crosslinking for 36 hours, and a new liquid crystal elastomer material can be obtained.
The catalyst is 1, 5-cyclooctadiene palladium dichloride.
The chiral cross-linking agent is prepared according to the following scheme:
adding 100 parts of tetrahydrofuran, 18 parts of triethylamine and 25 parts of chiral diphenol in parts by mass into a reaction kettle, and stirring for 30min at room temperature to dissolve uniformly; then adding 80 parts of diluted acyl chloride, dissolving in 200 parts of tetrahydrofuran, slowly adding into a reaction kettle, heating and controlling the temperature to 60 ℃, and reacting for 18 hours; after the reaction is finished, pouring the system into 600 parts of water for precipitation, then filtering, washing the system to be neutral by water, and drying the system to obtain the chiral cross-linking agent.
The diluted acyl chloride is undecylenic chloride.
The chiral diphenol is (R) -spiro diphenol.
The 50mg elastomer shrinkage set force of the test sample produced is 14.7X 10-3N, glass transition temperature 65.7 ℃.
Example 3
A preparation method of a new liquid crystal elastomer material adopts the following preparation technical scheme:
according to the mass parts, 136 parts of p-methoxybenzoic acid-4-allyloxy biphenyl monophenol ester, 26 parts of chiral cross-linking agent, 36 parts of polymethyl hydrogen-containing siloxane, 0.1 part of 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ], 0.1 part of 9, 9-diethylfluorene-2-boric acid, 0.5 part of 6-amino-2, 3-dihydroindene-1-ketone, 0.5 part of tris [ N, N-bis (trimethylsilane) amine ] erbium, 1.6 parts of polyaniline powder and 300 parts of toluene are added into a reaction kettle and stirred for 60min to be dissolved; then dissolving 0.15 part of catalyst by 3.5 parts of toluene, adding the solution into a reaction kettle, controlling the temperature at 60 ℃, reacting for 60min, then adding the material into a mold, ultrasonically treating for 20min to eliminate bubbles, and placing the mold into an oven at 80 ℃ to crosslink for 6h to form a film; after the film-formed elastomer is unidirectionally stretched by 50-70 percent, the elastomer is continuously placed into an oven at 80 ℃ for crosslinking for 48 hours, and the novel liquid crystal elastomer material can be obtained.
The catalyst is dichloro (1, 5-cyclooctadiene) platinum.
The chiral cross-linking agent is prepared according to the following scheme:
adding 120 parts of tetrahydrofuran, 26 parts of triethylamine and 35 parts of chiral diphenol in parts by mass into a reaction kettle, and stirring for 40min at room temperature to dissolve uniformly; then dissolving 100 parts of diluted acyl chloride in 300 parts of tetrahydrofuran, slowly adding the mixture into a reaction kettle, heating and controlling the temperature to 80 ℃, and reacting for 36 hours; after the reaction is finished, pouring the system into 800 parts of water for precipitation, then filtering, washing the system to be neutral by water, and drying the system to obtain the chiral cross-linking agent.
The dilute acyl chloride is 10-undecenoyl chloride or 8-methyl-6-noneoyl chloride.
The chiral diphenol is isosorbide.
Test specimens were made with a 50mg elastomer compression set force of 15.6X 10-3N, glass transition temperature 63.8 ℃.
Example 4
A preparation method of a new liquid crystal elastomer material adopts the following preparation technical scheme:
adding 124 parts by mass of p-methoxybenzoic acid-4-allyloxy biphenyl monophenol ester, 18 parts by mass of chiral cross-linking agent, 31 parts by mass of polymethylhydrosiloxane, 0.06 part by mass of 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ], 0.08 part by mass of 9, 9-diethylfluorene-2-boric acid, 0.05 part by mass of 6-amino-2, 3-dihydroindene-1-one, 0.05 part by mass of tris [ N, N-bis (trimethylsilane) amine ] erbium, 1.6 parts by mass of polyaniline powder and 300 parts by mass of toluene into a reaction kettle, and stirring for 60min to dissolve; then dissolving 0.15 part of catalyst by using 3.5 parts of toluene, adding the solution into a reaction kettle, controlling the temperature at 45 ℃, reacting for 60min, then adding the material into a mold, ultrasonically treating for 20min to eliminate bubbles, and placing the mold into a 65 ℃ oven to crosslink for 6h to form a film; after the film-formed elastomer is stretched unidirectionally by 50 percent, the elastomer is continuously placed into a drying oven at 65 ℃ for crosslinking for 38 hours, and a new liquid crystal elastomer material can be obtained.
The catalyst is (1, 5-cyclooctadiene) platinum dichloride.
The chiral cross-linking agent is prepared according to the following scheme:
adding 100 parts of tetrahydrofuran, 18 parts of triethylamine and 25 parts of chiral diphenol in parts by mass into a reaction kettle, and stirring for 30min at room temperature to dissolve uniformly; then, adding 80 parts of diluted acyl chloride, dissolving in 300 parts of tetrahydrofuran, slowly adding into a reaction kettle, heating and controlling the temperature to 80 ℃, and reacting for 36 hours; after the reaction is finished, pouring the system into 800 parts of water for precipitation, then filtering, washing the system to be neutral by water, and drying the system to obtain the chiral cross-linking agent.
The dilute acyl chloride is 8-methyl-6-nonenoyl chloride.
The chiral diphenol is isosorbide.
Test specimens were made with a 50mg elastomer compression set force of 15.1X 10-3N, glass transition temperature 63.9 ℃.
Example 5
A preparation method of a new liquid crystal elastomer material adopts the following preparation technical scheme:
adding 128 parts by mass of p-methoxybenzoic acid-4-allyloxy biphenyl monophenol ester, 19 parts by mass of chiral cross-linking agent, 32 parts by mass of polymethyl hydrogen-containing siloxane, 0.06 part by mass of 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ], 0.01 part by mass of 9, 9-diethylfluorene-2-boric acid, 0.3 part by mass of 6-amino-2, 3-dihydroindene-1-one, 0.2 part by mass of tris [ N, N-bis (trimethylsilane) amine ] erbium, 0.9 part by mass of polyaniline powder and 250 parts by mass of toluene into a reaction kettle, and stirring for 40min to dissolve; then dissolving 0.1 part of catalyst by 2.8 parts of toluene, adding the solution into a reaction kettle, controlling the temperature at 45 ℃, reacting for 34min, then adding the material into a mold, ultrasonically treating for 15min to eliminate bubbles, and placing the mold into a 65 ℃ oven to crosslink for 4h to form a film; and (3) after the film-formed elastomer is stretched in a unidirectional mode by 55%, continuously putting the film-formed elastomer into a 75 ℃ drying oven for crosslinking for 38 hours, and obtaining a new liquid crystal elastomer material.
The catalyst is 1, 5-cyclooctadiene palladium dichloride.
The chiral cross-linking agent is prepared according to the following scheme:
adding 110 parts of tetrahydrofuran, 22 parts of triethylamine and 28 parts of chiral diphenol in parts by mass into a reaction kettle, and stirring for 34min at room temperature to dissolve uniformly; then, dissolving 90 parts of diluted acyl chloride in 260 parts of tetrahydrofuran, slowly adding the mixture into a reaction kettle, heating and controlling the temperature to 65 ℃, and reacting for 18-36 hours; after the reaction is finished, pouring the system into 750 parts of water for precipitation, then filtering, washing the system to be neutral by water, and drying the system to obtain the chiral cross-linking agent.
The dilute acyl chloride is 5-norbornene-2-acyl chloride.
The chiral diphenol is isosorbide.
The 50mg elastomer shrinkage deformation force of the test sample produced is 13.8X 10-3N, glass transition temperature 64.2 ℃.
Comparative example 1
The procedure is as in example 1 except that no chiral crosslinking agent is added.
Test samples that could not be made.
Comparative example 2
The same procedure as in example 1 was repeated, except that the aniline powder was not added.
50mg of the resulting test sample has an elastomer compression set of 7.6X 10-3 N，The glass transition temperature was 52.7 ℃.
Comparative example 3
The procedure is as in example 1 except that 6-amino-2, 3-indan-1-one is not added.
The 50mg elastomer shrinkage set force of the test sample produced was 12.9X 10-3N, glass transition temperature 64.1 ℃.
Comparative example 4
The samples were not subjected to ultrasonic defoaming.
The 50mg elastomer shrinkage set force of the test sample produced was 12.2X 10-3N, glass transition temperature 64.1 ℃.
Comparative example 5
The procedure is as described in example 1 except that 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ] is not added.
The 50mg elastomer shrinkage set force of the test sample produced was 12.8X 10-3N, glass transition temperature 62.5 ℃.
Comparative example 6
Example 1 was repeated except that tris [ N, N-bis (trimethylsilanyl) amine ] erbium was not added.
The 50mg elastomer shrinkage deformation force of the test sample produced was 13.1X 10-3N, glass transition temperature 63.3 ℃.
Comparative example 7
Sample 9, 9-diethylfluorene-2-boronic acid was not used.
The 50mg elastomer shrinkage deformation force of the test sample produced was 13.2X 10-3N, glass transition temperature 63.8 ℃.
Claims (4)
1. A preparation method of a liquid crystal elastomer material adopts the following preparation technical scheme:
according to the mass portion, 124-136 portions of p-methoxybenzoic acid-4-allyloxy biphenyl monophenol ester, 18-26 portions of chiral cross-linking agent, 31-36 portions of polymethyl hydrogen-containing siloxane, 0.01-0.1 portion of 2-bromo-spiro [ 9H-fluorene-9, 9' - [9H ] xanthene ], 0.01-0.1 portion of 9, 9-diethyl fluorene-2-boric acid, 0.05-0.5 portion of 6-amino-2, 3-dihydroindene-1-one, 0.05-0.5 portion of tris [ N, N-bis (trimethylsilane) amine ] erbium, 0.8-1.6 portions of polyaniline powder and 200-300 portions of toluene are added into a reaction kettle and stirred for 30-60min to be dissolved; dissolving 0.05-0.15 part of catalyst by 2.5-3.5 parts of toluene, adding into a reaction kettle, controlling the temperature at 40-60 ℃, reacting for 30-60min, adding the material into a mold, ultrasonically treating for 10-20min to eliminate bubbles, and placing the mold into a drying oven at 60-80 ℃ to crosslink for 2-6h to form a film; after the film-formed elastomer is unidirectionally stretched by 50-70 percent, the film-formed elastomer is continuously placed into a drying oven at the temperature of 60-80 ℃ for crosslinking for 36-48h, and the novel liquid crystal elastomer material can be obtained.
2. The method for preparing a liquid crystal elastomer material according to claim 1, wherein: the catalyst is dichloro (1, 5-cyclooctadiene) platinum.
3. The method for preparing a liquid crystal elastomer material according to claim 1, wherein: the chiral cross-linking agent is prepared according to the following scheme:
adding 80-100 parts by mass of 8-methyl-6-nonenoyl chloride or undecylenyl chloride or 5-norbornene-2-acyl chloride, dissolving in 300 parts by mass of 200-membered and 10-membered tetrahydrofuran to prepare an acyl chloride solution, firstly adding 120 parts by mass of 100-membered and 120 parts by mass of tetrahydrofuran, 18-26 parts by mass of triethylamine and 25-35 parts by mass of chiral diphenol into a reaction kettle, and stirring for 30-40min at room temperature to dissolve uniformly; slowly adding the acyl chloride solution into a reaction kettle, heating to control the temperature to be 60-80 ℃, and reacting for 18-36 h; after the reaction is finished, pouring the system into 800 portions of 600-800 portions of water for precipitation, then filtering, washing with water to be neutral, and drying to obtain the chiral cross-linking agent.
4. The method for preparing a liquid crystal elastomer material according to claim 3, wherein: the chiral diphenol is 1, 1-binaphthyl-2, 2-diphenol.
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| CN101113200A (en) * | 2007-04-28 | 2008-01-30 | 中国科学院广州化学研究所 | Method for preparing backbone chain type liquid crystal elastomer |
| CN104529781A (en) * | 2014-11-14 | 2015-04-22 | 泰州市产品质量监督检验所 | A synthetic method of a chiral liquid crystal monomer, a cross-linking agent and an elastomer of the monomer |
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| CN101113200A (en) * | 2007-04-28 | 2008-01-30 | 中国科学院广州化学研究所 | Method for preparing backbone chain type liquid crystal elastomer |
| CN104529781A (en) * | 2014-11-14 | 2015-04-22 | 泰州市产品质量监督检验所 | A synthetic method of a chiral liquid crystal monomer, a cross-linking agent and an elastomer of the monomer |
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