CN110527071A - A kind of liquid crystal high polymer material and its synthetic method - Google Patents
A kind of liquid crystal high polymer material and its synthetic method Download PDFInfo
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
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Abstract
The present invention provides a kind of liquid crystal high polymer material and its synthetic method.Liquid crystal high polymer material of the invention is made of following composition: the structural unit derived from aromatic hydroxy-carboxylic, the structural unit derived from aromatic dicarboxylic acid, paracetamol, phenolphthalein, and molar percentage range shared by each component is followed successively by 60-85%, 7.5-20%, 3-19%, 1-4.5%.The present invention prepares liquid crystal polymer using paracetamol and phenolphthalein to substitute hydroquinone, due to the introducing of huge phenolphthalein side group, so that the liquid crystal polymer of preparation has good dissolubility, and it can obviously improve the processing performance of liquid crystal polymer, and the addition of paracetamol can also be improved the dissolubility of liquid crystal molecule.
Description
Technical field:
The present invention relates to a kind of liquid crystal high polymer material and its synthetic methods, belong to liquid crystal high polymer material technical field.
Background technique:
Liquid crystal polymer is the intermediate state polymer between solid crystal and liquid, although molecules align is unlike solid
The such three-dimensional order of crystalline state, but it is also not that liquid is unordered like that, but there is the order of certain (one-dimensional or two-dimentional).It is one
The novel high molecular material of kind, is generally presented liquid crystal liquid crystal property in molten state.This kind of material has excellent heat resistance and molding
Processing performance.Lyotropic Liquid Crystalline Polymer and thermotropic liquid crystal high polymer can be divided into again according to the condition of Formation of liquid crystals.The former
It is in liquid crystal state in solvent, the latter is in liquid crystal state because of temperature change.Current existing patent by be added the distorted-structures such as naphthalene nucleus come
The linear of copolyesters rigid chain is destroyed, the rigidity of strand entirety is reduced and comes to reduce fusing point or the flexible structures such as phenylate are added
Fusing point is reduced, the phenolphthalein structure in the present invention can reduce fusing point, while can also improve the problem of liquid crystal polymer dissolubility difference.
Summary of the invention:
The purpose of the present invention is providing a kind of liquid crystal high polymer material and its synthetic method in view of the above problems, using pair
Paracetamol prepares liquid crystal polymer with phenolphthalein to substitute hydroquinone, due to the introducing of huge phenolphthalein side group, so that preparation
Liquid crystal polymer there is good dissolubility, and can obviously improve the processing performance of liquid crystal polymer, and to acetyl ammonia
The addition of base phenol can also be improved the dissolubility of liquid crystal molecule.
Above-mentioned purpose is realized by following technical scheme:
A kind of liquid crystal high polymer material is made of following composition: structural unit derived from aromatic hydroxy-carboxylic, derived from virtue
Structural unit, paracetamol, the phenolphthalein of fragrant race's dicarboxylic acids, molar percentage range shared by each component be followed successively by 60-85%,
7.5-20%、3-19%、1-4.5%。
The liquid crystal high polymer material, the structural unit derived from aromatic hydroxy-carboxylic are 4 '-xenols
Base -4- carboxylic acid, 6-Hydroxy-2-naphthoic acid, P-hydroxybenzoic acid one or any of several compounding, preferably P-hydroxybenzoic acid.
The liquid crystal high polymer material, the structural unit derived from aromatic dicarboxylic acid be terephthalic acid (TPA), 1,
1 '-biphenyl -3,4 '-dicarboxylic acids, 1,1 '-biphenyl -3,3 '-dicarboxylic acids, 1,6- naphthalenedicarboxylic acid, 1,7- naphthalenedicarboxylic acid, 2,7- naphthalene two
One of formic acid, 4,4- diphenyl ether dicarboxylic acid, 1,3- propane dicarboxylic acids, 1,4- butane dicarboxylic acid, 1,5- pentanedicarboxylic acid or
Any several compoundings, preferably terephthalic acid (TPA).
The synthetic method of above-mentioned liquid crystal high polymer material, this method comprises the following steps:
(1) structural unit, the acetparaminosalol for being derived from aromatic hydroxy-carboxylic acylation reaction: is added in a kettle according to the ratio
Phenol, phenolphthalein carry out acylation reaction with acetic anhydride respectively under the effect of the catalyst；
(2) ester exchange reaction: by the structural unit derived from aromatic hydroxy-carboxylic acylated in step (1), acetparaminosalol
Phenol, phenolphthalein are proportionally added into the structural unit derived from aromatic dicarboxylic acid and carry out ester exchange reaction system under the action of catalyst
Standby liquid crystal polymer.
The synthetic method of the liquid crystal high polymer material, from aromatic series hydroxyl derived from acylation reaction in the step (1)
The structural unit of yl carboxylic acid, paracetamol, phenolphthalein and acetic anhydride molar ratio be respectively 1:1:1:4.8, in acylation reaction
The sum of hydroxy radical content in structural unit, paracetamol, phenolphthalein derived from aromatic hydroxy-carboxylic rubs with acetic anhydride
You are than being 1:1.2.
The synthetic method of the liquid crystal high polymer material, the catalyst in the step (1) select peroxophosphoric acid, fluoroform
One of sulfonic acid, sulfamic acid, pyridine, 1- methylpyrrole, p-methyl benzenesulfonic acid, 4- lutidines are several groups any
It closes.
The synthetic method of the liquid crystal high polymer material, the acylation reaction of the step (1) is in the process by being passed through nitrogen
Gas removes by-product acetic acid, pours into be precipitated in ice water by product after reaction and precipitate, is filtered, washed, drying.
The specific method of the synthetic method of the liquid crystal high polymer material, the ester exchange reaction of the step (2) is: will
The acylated structural unit derived from aromatic hydroxy-carboxylic, paracetamol, phenolphthalein, are proportionally added into and spread out in step (1)
The structural unit for being born from aromatic dicarboxylic acid carries out ester exchange reaction under the action of catalyst, is first warming up to 120 DEG C and stops 30
Minute, reaction is then started to warm up, while logical nitrogen removes by-product acetic acid, turns when reaction solution switchs to clarification again by white
It when becoming muddiness, further heats up, and accelerates mixing speed, after reacting 2-5h, continue to heat up, start simultaneously at and vacuumize removal vinegar
Acid, temperature more condition of high vacuum degree is bigger, and when being warming up to 360-380 DEG C, vacuum degree reaches 70 pas, observes and extracts out without obvious acetic acid
Shi Fanying terminates, and extrudes material, cooling and dicing with nitrogen.
The synthetic method of the liquid crystal high polymer material, used catalyst is in ester exchange reaction in the step (2)
Sodium acetate, 1- methylimidazole, magnesium acetate, stannous acetate, lead acetate, butyl titanate, N, N- dimethyl aminopyridine, three oxidations
One of antimony, potassium acetate, zinc acetate or any several compoundings.
The synthetic method of the liquid crystal high polymer material, used catalyst is used in ester exchange reaction in the step (2)
Amount accounts for a ten thousandth of monomeric charge gross mass.
The utility model has the advantages that
The present invention utilizes the side group structure of phenolphthalein, can increase steric hindrance, to reduce the fusing point of product, and improve liquid crystal height
The dissolubility of molecule, and the addition of paracetamol also increases significantly to dissolubility, helps to solve the prior art
The liquid crystal polymer of preparation has dystectic problem.
Specific embodiment:
A kind of liquid crystal high polymer material of the invention, is made of following composition: structural unit derived from aromatic hydroxy-carboxylic,
Structural unit, paracetamol, phenolphthalein derived from aromatic dicarboxylic acid, molar percentage range shared by each component are followed successively by
60-85%、7.5-20%、3-19%、1-4.5%。
The liquid crystal high polymer material, the structural unit derived from aromatic hydroxy-carboxylic are 4 '-xenols
Base -4- carboxylic acid, 6-Hydroxy-2-naphthoic acid, P-hydroxybenzoic acid one or any of several compounding, preferably P-hydroxybenzoic acid.
The liquid crystal high polymer material, the structural unit derived from aromatic dicarboxylic acid be terephthalic acid (TPA), 1,
1 '-biphenyl -3,4 '-dicarboxylic acids, 1,1 '-biphenyl -3,3 '-dicarboxylic acids, 1,6- naphthalenedicarboxylic acid, 1,7- naphthalenedicarboxylic acid, 2,7- naphthalene two
One of formic acid, 4,4- diphenyl ether dicarboxylic acid, 1,3- propane dicarboxylic acids, 1,4- butane dicarboxylic acid, 1,5- pentanedicarboxylic acid or
Any several compoundings, preferably terephthalic acid (TPA).
The synthetic method of above-mentioned liquid crystal high polymer material, this method comprises the following steps:
(1) structural unit, the acetparaminosalol for being derived from aromatic hydroxy-carboxylic acylation reaction: is added in a kettle according to the ratio
Phenol, phenolphthalein carry out acylation reaction with acetic anhydride respectively under the effect of the catalyst；
(2) ester exchange reaction: by the structural unit derived from aromatic hydroxy-carboxylic acylated in step (1), acetparaminosalol
Phenol, phenolphthalein are proportionally added into the structural unit derived from aromatic dicarboxylic acid and carry out ester exchange reaction system under the action of catalyst
Standby liquid crystal polymer.
The synthetic method of the liquid crystal high polymer material, from aromatic series hydroxyl derived from acylation reaction in the step (1)
The structural unit of yl carboxylic acid, paracetamol, phenolphthalein and acetic anhydride molar ratio be respectively 1:1:1:4.8, in acylation reaction
The sum of hydroxy radical content in structural unit, paracetamol, phenolphthalein derived from aromatic hydroxy-carboxylic rubs with acetic anhydride
You are than being 1:1.2.
The synthetic method of the liquid crystal high polymer material, the catalyst in the step (1) select peroxophosphoric acid, fluoroform
One of sulfonic acid, sulfamic acid, pyridine, 1- methylpyrrole, p-methyl benzenesulfonic acid, 4- lutidines are several groups any
It closes.
The synthetic method of the liquid crystal high polymer material, the acylation reaction of the step (1) is in the process by being passed through nitrogen
Gas removes by-product acetic acid, pours into be precipitated in ice water by product after reaction and precipitate, is filtered, washed, drying.
The specific method of the synthetic method of the liquid crystal high polymer material, the ester exchange reaction of the step (2) is: will
The acylated structural unit derived from aromatic hydroxy-carboxylic, paracetamol, phenolphthalein, are proportionally added into and spread out in step (1)
The structural unit for being born from aromatic dicarboxylic acid carries out ester exchange reaction under the action of catalyst, is first warming up to 120 DEG C and stops 30
Minute, reaction is then started to warm up, while logical nitrogen removes by-product acetic acid, turns when reaction solution switchs to clarification again by white
It when becoming muddiness, further heats up, and accelerates mixing speed, after reacting 2-5h, continue to heat up, start simultaneously at and vacuumize removal vinegar
Acid, temperature more condition of high vacuum degree is bigger, and when being warming up to 360-380 DEG C, vacuum degree reaches 70 pas, observes and extracts out without obvious acetic acid
Shi Fanying terminates, and extrudes material, cooling and dicing with nitrogen.
The synthetic method of the liquid crystal high polymer material, used catalyst is in ester exchange reaction in the step (2)
Sodium acetate, 1- methylimidazole, magnesium acetate, stannous acetate, lead acetate, butyl titanate, N, N- dimethyl aminopyridine, three oxidations
One of antimony, potassium acetate, zinc acetate or any several compoundings.
The synthetic method of the liquid crystal high polymer material, used catalyst is used in ester exchange reaction in the step (2)
Amount accounts for a ten thousandth of monomeric charge gross mass.
Illustrate method and effect of the invention below by way of specific embodiment:
Embodiment 1
Take 60 moles of P-hydroxybenzoic acid, 18 moles of paracetamol, 2 moles of phenolphthalein respectively at acetic anhydride in catalyst pyridine
Under the action of carry out acylation reaction, during the reaction by be passed through nitrogen remove by-product acetic acid, after reaction by product
It pours into and precipitating is precipitated in ice water, filtered, washed, drying.
In the reaction kettle with logical nitrogen and condenser, be added it is acylated after P-hydroxybenzoic acid, paracetamol,
Phenolphthalein, 20 moles of terephthalic acid (TPA) polymerize under the action of catalyst acetic acid zinc, be first warming up to 120 DEG C stop 30
Minute, reaction is then started to warm up, while logical nitrogen removes by-product acetic acid, turns when reaction solution switchs to clarification again by white
It when becoming muddiness, further heats up, reaction after a certain period of time, continues to heat up, and accelerate mixing speed, starts simultaneously at and vacuumize shifting
Except acetic acid, temperature more condition of high vacuum degree is bigger, and when being warming up to 360-380 DEG C, vacuum degree reaches 70 pas, observes without obvious vinegar
Reaction terminates when acid extraction, extrudes material, cooling and dicing with nitrogen, the fusing point through detecting final liquid crystal polymer obtained is
263 DEG C, the mass fraction dissolved in solvent N-methyl pyrilidone is 26%.
Embodiment 2
The present embodiment and embodiment 1 the difference is that, the dosage of each monomer is 70 moles of 6-Hydroxy-2-naphthoic acid, right
17 moles of Paracetamol, 3 moles of phenolphthalein, 10 moles of 1,3- propane dicarboxylic acids, through detecting final liquid crystal polymer obtained
Fusing point is 276 DEG C, and the mass fraction dissolved in solvent N-methyl pyrilidone is 27%.
Embodiment 3
The present embodiment and embodiment 1 the difference is that, the dosage of each monomer is 80 moles of 6-Hydroxy-2-naphthoic acid, right
6 moles of Paracetamol, 4 moles of phenolphthalein, 10 moles of 4,4- diphenyl ether dicarboxylic acid, through detecting final liquid crystal polymer obtained
Fusing point is 272 DEG C, and the mass fraction dissolved in solvent N-methyl pyrilidone is 21%.
Embodiment 4
The present embodiment and embodiment 1 the difference is that, the dosage of each monomer is that 4 '-Hydroxybiphenyl -4- carboxylic acids 65 rub
It is high to be detected final liquid crystal obtained for that, 15.5 moles of paracetamol, 4.5 moles of phenolphthalein, 15 moles of 2,7- naphthalenedicarboxylic acid
The fusing point of molecule is 269 DEG C, and the mass fraction dissolved in solvent N-methyl pyrilidone is 29%.
Embodiment 5
The present embodiment and embodiment 1 the difference is that, the dosage of each monomer is that 4 '-Hydroxybiphenyl -4- carboxylic acids 75 rub
That, 11 moles of paracetamol, 4 moles of phenolphthalein, 1,1 '-biphenyl -3,3 ' -10 moles of dicarboxylic acids are detected final obtained
The fusing point of liquid crystal polymer is 263 DEG C, and the mass fraction dissolved in solvent N-methyl pyrilidone is 24%.
Comparative example 1
The present embodiment and embodiment 1 the difference is that, the dosage of each monomer is 60 moles of P-hydroxybenzoic acid, to benzene two
20 moles of phenol, 20 moles of terephthalic acid (TPA), the fusing point through detecting final liquid crystal polymer obtained is 337 DEG C, in solvent N- first
The mass fraction dissolved in base pyrrolidones is 18%.
Comparative example 2
The present embodiment and embodiment 1 the difference is that, the dosage of each monomer is 80 moles of 6-Hydroxy-2-naphthoic acid, right
10 moles of benzenediol, 10 moles of 4,4- diphenyl ether dicarboxylic acid, the fusing point through detecting final liquid crystal polymer obtained is 303 DEG C,
The mass fraction dissolved in solvent N-methyl pyrilidone is 17%.
The fusing point of the liquid crystal polymer measured from the above comparative example and embodiment can be seen that in same reaction condition
Under, the present invention prepares liquid crystal polymer using paracetamol and phenolphthalein to substitute hydroquinone, due to huge phenolphthalein side group
Introducing and can obviously improve the processability of liquid crystal polymer so that the liquid crystal polymer of preparation has good dissolubility
Can, and the addition of paracetamol can also be improved the dissolubility of liquid crystal molecule.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Made any modifications, equivalent replacements, and improvements etc., should all be included in the protection scope of the present invention within mind and principle.
Claims (10)
1. a kind of liquid crystal high polymer material, which is characterized in that the liquid crystal high polymer material is made of following composition: derived from fragrance
The structural unit of race's hydroxycarboxylic acid, the structural unit derived from aromatic dicarboxylic acid, paracetamol, phenolphthalein, each component institute
It accounts for molar percentage range and is followed successively by 60-85%, 7.5-20%, 3-19%, 1-4.5%.
2. liquid crystal high polymer material according to claim 1, which is characterized in that described derived from aromatic hydroxy-carboxylic
Structural unit is that 4 '-Hydroxybiphenyl -4- carboxylic acids, 6-Hydroxy-2-naphthoic acid, P-hydroxybenzoic acid one or any of several are multiple
Match, preferably P-hydroxybenzoic acid.
3. liquid crystal high polymer material according to claim 1, which is characterized in that the knot derived from aromatic dicarboxylic acid
Structure unit be terephthalic acid (TPA), 1,1 '-biphenyl -3,4 '-dicarboxylic acids, 1,1 '-biphenyl -3,3 '-dicarboxylic acids, 1,6- naphthalenedicarboxylic acid,
1,7- naphthalenedicarboxylic acid, 2,7- naphthalenedicarboxylic acid, 4,4- diphenyl ether dicarboxylic acid, 1,3- propane dicarboxylic acids, 1,4- butane dicarboxylic acid, 1,5-
One of pentanedicarboxylic acid or any several compoundings, preferably terephthalic acid (TPA).
4. the synthetic method of liquid crystal high polymer material described in a kind of one of claim 1-3, which is characterized in that this method includes such as
Lower step:
(1) structural unit, the acetparaminosalol for being derived from aromatic hydroxy-carboxylic acylation reaction: is added in a kettle according to the ratio
Phenol, phenolphthalein carry out acylation reaction with acetic anhydride respectively under the effect of the catalyst；
(2) ester exchange reaction: by the structural unit derived from aromatic hydroxy-carboxylic acylated in step (1), acetparaminosalol
Phenol, phenolphthalein are proportionally added into the structural unit derived from aromatic dicarboxylic acid and carry out ester exchange reaction system under the action of catalyst
Standby liquid crystal polymer.
5. the synthetic method of liquid crystal high polymer material according to claim 4, which is characterized in that acyl in the step (1)
Change and distinguishes derived from reaction from the molar ratio of the structural unit of aromatic hydroxy-carboxylic, paracetamol, phenolphthalein and acetic anhydride
For 1:1:1:4.8, from the hydroxyl in the structural unit, paracetamol, phenolphthalein of aromatic hydroxy-carboxylic derived from acylation reaction
The sum of base content and the molar ratio of acetic anhydride are 1:1.2.
6. the synthetic method of liquid crystal high polymer material according to claim 4, which is characterized in that in the step (1)
Catalyst selects peroxophosphoric acid, trifluoromethanesulfonic acid, sulfamic acid, pyridine, 1- methylpyrrole, p-methyl benzenesulfonic acid, 4- dimethyl pyrazole
One of pyridine or any several combinations.
7. the synthetic method of liquid crystal high polymer material according to claim 4, which is characterized in that the acyl of the step (1)
Change in reaction process and remove by-product acetic acid by being passed through nitrogen, pours into be precipitated in ice water by product after reaction and precipitate, it will
It is filtered, and is washed, drying.
8. the synthetic method of liquid crystal high polymer material according to claim 4, which is characterized in that the ester of the step (2)
The specific method of exchange reaction is: by the structural unit derived from aromatic hydroxy-carboxylic acylated in step (1), to acetyl ammonia
Base phenol, phenolphthalein are proportionally added into the structural unit derived from aromatic dicarboxylic acid and carry out ester exchange reaction under the action of catalyst,
It is first warming up to 120 DEG C and stops 30 minutes, then start to warm up reaction, while logical nitrogen removes by-product acetic acid, works as reaction solution
It when being changed into muddiness switching to clarification again by white, further heats up, and accelerate mixing speed, after reacting 2-5h, after of continuing rising
Temperature starts simultaneously at and vacuumizes removal acetic acid, and temperature more condition of high vacuum degree is bigger, and when being warming up to 360-380 DEG C, vacuum degree reaches 70
Pa, reaction terminates when observing without the extraction of obvious acetic acid, extrudes material, cooling and dicing with nitrogen.
9. the synthetic method of liquid crystal high polymer material according to claim 4, which is characterized in that ester in the step (2)
In exchange reaction used catalyst be sodium acetate, 1- methylimidazole, magnesium acetate, stannous acetate, lead acetate, butyl titanate, N,
One of N- dimethyl aminopyridine, antimony trioxide, potassium acetate, zinc acetate or any several compoundings.
10. the synthetic method of liquid crystal high polymer material according to claim 4, which is characterized in that ester in the step (2)
Used catalyst dosage accounts for a ten thousandth of monomeric charge gross mass in exchange reaction.
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| CN113980431A (en) * | 2021-12-01 | 2022-01-28 | 南京清研高分子新材料有限公司 | High-performance liquid crystal polymer film material and preparation method thereof |
| CN114853992A (en) * | 2022-04-26 | 2022-08-05 | 四川大学 | Soluble low-dielectric-constant low-dielectric-loss flame-retardant full-aromatic copolyester and preparation method and application thereof |
| CN115322352A (en) * | 2022-08-01 | 2022-11-11 | 武汉科技大学 | Preparation and application of liquid crystal polymer based on 6-hydroxy-2-naphthoic acid derivative |
| US12035467B2 (en) | 2020-02-26 | 2024-07-09 | Ticona Llc | Circuit structure |
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| CN103342804A (en) * | 2013-07-23 | 2013-10-09 | 南通海迪化工有限公司 | Thermotropic liquid crystal polymer material and synthesis method thereof |
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| CN103342804A (en) * | 2013-07-23 | 2013-10-09 | 南通海迪化工有限公司 | Thermotropic liquid crystal polymer material and synthesis method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US12035467B2 (en) | 2020-02-26 | 2024-07-09 | Ticona Llc | Circuit structure |
| CN113980431A (en) * | 2021-12-01 | 2022-01-28 | 南京清研高分子新材料有限公司 | High-performance liquid crystal polymer film material and preparation method thereof |
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| CN114853992A (en) * | 2022-04-26 | 2022-08-05 | 四川大学 | Soluble low-dielectric-constant low-dielectric-loss flame-retardant full-aromatic copolyester and preparation method and application thereof |
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