CN111234218B - Preparation method of soluble polyimide containing amino phenylsulfonyl hexafluoropropane structure - Google Patents
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Abstract
The invention discloses a preparation method of soluble polyimide containing an aminophenylsulfonyl hexafluoropropane structure. The soluble polyimide containing the amino-phenyl sulfone hexafluoropropane structure is prepared by adopting diamine containing the amino-phenyl sulfone hexafluoropropane and aromatic dianhydride through a two-step reaction, and the structural formula of the soluble polyimide is as follows:
. The polyimide material of the invention has excellent solubility, excellent heat resistance and mechanical property, and good optical property, and the thin polymer has application value in transportation, electronic and electric appliances.
Description
Technical Field
The invention belongs to the field of high polymer material science, and particularly relates to a preparation method of soluble polyimide containing an aminophenylsulfonyl hexafluoropropane structure.
Background
Polyimide (PI) is a high-performance polymer containing an imide ring structure in a molecular structure, has excellent comprehensive performance, and is widely applied to the fields of aviation, aerospace, microelectronics, separation membranes and the like. However, due to the rigid main chain structure, strong interaction among molecules and close packing of molecular chains, the solubility of the resin is poor, the processing temperature is high, and the molding processing of the resin is difficult. In addition, most of the conventional polyimides have a deep color and poor optical transparency due to high aromatic conjugation of the molecular main chain and charge transfer interaction in the molecular chain. In order to overcome the above difficulties, many researchers improve the related properties of polyimide by introducing an asymmetric structure, a large substituent side group, a flexible bond and a non-coplanar structure into the main chain of polyimide through molecular design. Soluble polyimides have been the focus of recent research. Because fluorine atoms have higher electronegativity, lower molar polarizability and stronger hydrophobicity, the introduction of the fluorine atoms into polyimide can endow the polyimide with good functional performance hydrophobicity, and because of the steric hindrance effect of fluorine groups, the PI has better solubility, thereby improving the processing performance of the polyimide.
Sulfone group and fluorine are introduced into a polyimide structure through molecular design to prepare the soluble polyimide. The sulfone group and the fluorine are introduced into the polyimide structure, so that the solubility, the thermal stability, the low humidity and the high friction resistance of the polyimide are effectively improved, and the high thermal stability and the good friction property of the matrix resin are endowed by the strong polar action of the sulfone group. Therefore, the polyimide resin can be dissolved in a high-boiling-point organic solvent and can be well dissolved in a low-boiling-point solvent, so that the low-temperature curing of the insoluble polyimide becomes possible. The polyimide material also has excellent thermal property, optical property, dielectric property, friction resistance and the like. The polyimide containing fluorine and a sulfone group structure is obtained through molecular design, and the material has potential application in the application fields of aerospace, microelectronics, photoelectrons, friction and the like.
Disclosure of Invention
The invention aims to provide a preparation method of soluble polyimide containing an amino phenylsulfonyl hexafluoropropane structure.
The method comprises the following specific steps:
(1) Under the protection of nitrogen, dissolving equimolar diamine monomer and aromatic dianhydride monomer containing amido benzenesulfonyl hexafluoropropane in a polar solvent N-methyl pyrrolidone (NMP), enabling the solid content of the monomers in a reaction system to be 10% -20%, introducing nitrogen at room temperature, and stirring for 24 hours to obtain a precursor polyamide acid (PAA) viscous solution.
(2) Dissolving the polyamic acid viscous solution prepared in the step (1) by using N-methyl pyrrolidone, casting on a clean glass plate, drying at 80 ℃ in vacuum overnight, then putting the glass plate carrying the polyamic acid into a muffle furnace for temperature programming, heating at 120 ℃, 150 ℃, 180 ℃, 200 ℃, 250 ℃ and 300 ℃ for 1 hour respectively, demoulding by using distilled water after cooling, and drying to obtain a light yellow soft polyimide film, namely the soluble polyimide containing the amino-phenylsulfonyl hexafluoropropane structure, wherein the structural formula is as follows:
wherein Ar is one of the following 15 aromatic structures
The chemical name of the diamine monomer containing the aminophenylsulfonyl hexafluoropropane is 2, 2-bis [4- (4-aminophenylsulfonyl) phenyl ] hexafluoropropane, and the structural formula of the diamine monomer is as follows:
the aromatic dianhydride is one of 3,3 ', 4,4' -pyromellitic dianhydride, 3,3 ', 4,4' -biphenyltetracarboxylic dianhydride, 3,3 ', 4,4' -diphenyl ether tetracarboxylic dianhydride, 3,3 ', 4,4' -benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4' -diphenyl sulfide tetracarboxylic dianhydride, 3,3 ', 4,4' -diphenyl sulfone tetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, 2,2-bis [4- (3,4-dicarboxyphenoxy) phenyl ] hexafluoropropane dianhydride, 1, 4-bis (3,4-dicarboxyphenoxy) -2,2 ', 3-trimethylbenzene dianhydride, 1, 4-bis (3,4-dicarboxyphenoxy) -2,3 ' -di-tert-butyl-benzene dianhydride, 4' -dimethyl (3, 4' -dimethyl-phenyl) -1, 3 ' -dimethyl (3, 4' -dimethyl-3 ' -methyl-phenyl) dianhydride, and 1, 4' -dimethyl-3 ' -dimethyl-phenyl dianhydride.
The invention has the advantages that:
(1) The soluble polyimide containing the amino phenylsulfonyl hexafluoropropane structure can be dissolved in a high-boiling-point organic solvent N, N '-Dimethylformamide (DMF) and N, N' -dimethylacetamide (DMAc)N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), and Tetrahydrofuran (THF) and chloroform (CHCl) which are low-boiling solvents 3 ) Dichloromethane (CH) 2 Cl 2 ) And acetone, which makes it possible to fix the polyimide, which is difficult to dissolve, at low temperature. The polyimide material also has excellent thermal property, friction property and the like. In terms of thermal properties, the glass transition temperature (T) is somewhat lowered, although the thermal properties are somewhat lowered, as compared with commercial polyimides g ) The material still keeps above 270 ℃ and the temperature of 10 percent of thermal decomposition is above 500 ℃, and the material can meet the use requirements in the application fields of aerospace, friction, microelectronics, photoelectrons and the like.
(2) The soluble polyimide containing the amino phenylsulfonyl hexafluoropropane structure has good thermal property and glass transition temperature (T) g ) The temperature ranges of 270 to 329 ℃ and 10 percent of thermal weight loss are 519 to 528 ℃ respectively, and the carbon residue rate at 800 ℃ is more than 52 percent.
(3) The contact angle range of the novel polyimide is 82.4-95.0 degrees, and the values of the novel polyimide are all higher than that of a commercial Kapton film (81.6 degrees).
Drawings
Fig. 1 is a structural formula of soluble polyimide containing an aminophenylsulfone-based hexafluoropropane structure prepared in example 1 of the present invention.
Fig. 2 is a structural formula of the soluble polyimide containing an aminophenylsulfone-based hexafluoropropane structure prepared in example 2 of the present invention.
Fig. 3 is a structural formula of the soluble polyimide containing an aminophenylsulfone-based hexafluoropropane structure prepared in example 3 of the present invention.
Fig. 4 is a structural formula of the soluble polyimide containing an aminophenylsulfone-based hexafluoropropane structure prepared in example 4 of the present invention.
Fig. 5 is a structural formula of the soluble polyimide containing an aminophenylsulfone-based hexafluoropropane structure prepared in example 5 of the present invention.
Fig. 6 is an infrared spectrum of the soluble polyimide containing an aminophenylsulfone-based hexafluoropropane structure prepared in examples 1 to 5 of the present invention.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1:
2, 2-bis [4- (4-aminophenylsulfonyl) phenyl ] was placed in a 50 mL two-necked flask with nitrogen inlet and outlet and magnetic stirring]Hexafluoropropane (1.0662 g,1.734 mmol) and refined NMP (6.81 g, solids content 17.5%), stirring for 1h under nitrogen protection, adding 3,3 ', 4,4' -pyromellitic dianhydride (0.3784 g,1.734 mmol) 3 times, ensuring complete dissolution of the first addition before each dianhydride addition, and reacting at room temperature for 24h after all additions to give a viscous polyamic acid (PAA) solution. Preparing PAA solution with solid content of about 10-20 wt% by using NMP solvent at 6X 6 cm 2 And 3X 3 cm 2 And (2) forming a film on a glass plate, standing overnight at 80 ℃, raising the temperature in a muffle furnace by programs at 120 ℃, 150 ℃, 180 ℃, 200 ℃, 250 ℃ and 300 ℃ for 1 hour respectively, and after cooling, putting the film into water for demoulding to obtain the polyimide film, namely the soluble polyimide containing the amino phenyl sulfone hexafluoropropane structure.
Example 2:
2, 2-bis [4- (4-aminophenylsulfonyl) phenyl is added into a 50 mL two-mouth bottle with a nitrogen inlet and a nitrogen outlet and magnetic stirring]Hexafluoropropane (0.5314 g,0.8647 mmol) and refined NMP (4.12 g, 16% solids) were stirred under nitrogen for 1h, then 3,3, 4' -biphenyltetracarboxylic dianhydride (0.2544 g,0.8647 mmol) was added in portions, complete dissolution of the first addition was ensured before each dianhydride addition, and after all additions, reaction was carried out at room temperature for 24h to give a viscous polyamic acid (PAA) solution. Preparing PAA solution with solid content of about 10 to 20wt% by using NMP solvent at 6 x 6 cm 2 And 3X 3 cm 2 Film formation on glass plates, 80 ℃ overnight, schedule HeatThe temperature is 120 ℃, 150 ℃, 180 ℃, 200 ℃, 250 ℃ and 300 ℃ for 1h respectively, and after cooling, the polyimide film is put into water for demoulding to obtain the polyimide film, namely the soluble polyimide containing the amino phenylsulfonyl hexafluoropropane structure.
Example 3:
2, 2-bis [4- (4-aminophenylsulfonyl) phenyl is added into a 50 mL two-mouth bottle with a nitrogen inlet and a nitrogen outlet and magnetic stirring]Hexafluoropropane (0.6901 g,1.1229 mmol) and refined NMP (5.28 g, solids content 16.8%), stirring under nitrogen for 1h, adding 3,3 ', 4' -diphenyl ether tetracarboxylic dianhydride (0.3483 g,1.1229 mmol) in portions, ensuring complete dissolution of the first addition before each dianhydride addition, reacting at room temperature for 24h after all additions, and reacting at room temperature for 24h to obtain a viscous polyamic acid (PAA) solution. Preparing PAA solution with solid content of about 10-20 wt% by using NMP solvent at 6X 6 cm 2 And 3X 3 cm 2 And (2) forming a film on a glass plate, standing overnight at 80 ℃, carrying out temperature programming in a muffle furnace at 120 ℃, 150 ℃, 180 ℃, 200 ℃, 250 ℃ and 300 ℃ for 1 hour respectively, cooling, and then putting the film into water for demoulding to obtain a polyimide film, namely the soluble polyimide containing the amino-phenylsulfonyl-hexafluoropropane structure.
Example 4:
2, 2-bis [4- (4-aminophenylsulfonyl) phenyl is added into a 50 mL two-mouth bottle with a nitrogen inlet and a nitrogen outlet and magnetic stirring]Hexafluoropropane (0.4385 g,0.7135 mmol) and refined NMP (3.29 g, solids content 16.8%) were stirred under nitrogen for 1h, then 3,3 ', 4,4' -benzophenone tetracarboxylic dianhydride (0.2299 g,0.7135 nmol) was added in portions, complete dissolution of the first addition was ensured before each dianhydride addition, and after all additions, reaction was continued for 24h at room temperature followed by 24h at room temperature to give a viscous polyamic acid (PAA) solution. Preparing a PAA solution with the solid content of about 10 to 20wt% by using NMP solvent at the concentration of 6 multiplied by 6 cm 2 And 3X 3 cm 2 Forming a film on a glass plate, standing overnight at 80 ℃, raising the temperature in a muffle furnace by programs at 120 ℃, 150 ℃, 180 ℃, 200 ℃, 250 ℃ and 300 ℃ for 1 hour respectively, cooling, and then putting the polyimide film into water for demoulding to obtain the polyimide film, namely the amino-containing phenylsulfonyl hexafluoropropanolSoluble polyimide with an alkane structure.
Example 5:
2, 2-bis [4- (4-aminophenylsulfonyl) phenyl is added into a 50 mL two-mouth bottle with a nitrogen inlet and a nitrogen outlet and magnetic stirring]Hexafluoropropane (0.4313 g,0.7018 nmol) and refined NMP (3.60 g, 20% solids) were stirred under nitrogen for 1h, then 2, 2-bis (3, 4-dicarboxyphenyl) propane dianhydride (0.3116 g,0.7018 nmol) was added in portions, complete dissolution of the first addition was ensured before each dianhydride addition, and after all addition, reaction was continued for 24h at room temperature, followed by further reaction for 24h at room temperature to give a viscous polyamic acid (PAA) solution. Preparing PAA solution with solid content of about 10 to 20wt% by using NMP solvent at 6 x 6 cm 2 And 3X 3 cm 2 And (2) forming a film on a glass plate, standing overnight at 80 ℃, carrying out temperature programming in a muffle furnace at 120 ℃, 150 ℃, 180 ℃, 200 ℃, 250 ℃ and 300 ℃ for 1 hour respectively, cooling, and then putting the film into water for demoulding to obtain the polyimide film, namely the soluble polyimide containing the amino-phenylsulfonyl-hexafluoropropane structure.
Claims (1)
1. A preparation method of soluble polyimide containing an amino phenylsulfonyl hexafluoropropane structure is characterized by comprising the following specific steps:
(1) Under the protection of nitrogen, dissolving equimolar diamine monomer and aromatic dianhydride monomer containing aminophenylsulfone hexafluoropropane in a polar solvent N-methyl pyrrolidone, leading the total amount of the monomers in a reaction system to be 10-20 percent of solid content, introducing nitrogen at room temperature and stirring for 24 hours to prepare precursor polyamide acid viscous solution;
(2) Dissolving the polyamic acid viscous solution prepared in the step (1) by using N-methyl pyrrolidone, casting on a clean glass plate, drying at 80 ℃ in vacuum overnight, then putting the glass plate carrying the polyamic acid into a muffle furnace for temperature programming, heating at 120 ℃, 150 ℃, 180 ℃, 200 ℃, 250 ℃ and 300 ℃ for 1 hour respectively, demoulding by using distilled water after cooling, and drying to obtain a light yellow soft polyimide film, namely the soluble polyimide containing the amino-phenylsulfonyl hexafluoropropane structure, wherein the structural formula is as follows:
wherein Ar is one of the following 15 aromatic structures
The chemical name of the diamine monomer containing the aminophenylsulfonyl hexafluoropropane is 2, 2-bis [4- (4-aminophenylsulfonyl) phenyl ] hexafluoropropane, and the structural formula is as follows:
the aromatic dianhydride is one of 3,3 ', 4,4' -pyromellitic dianhydride, 3,3 ', 4,4' -biphenyltetracarboxylic dianhydride, 3,3 ', 4,4' -diphenyl ether tetracarboxylic dianhydride, 3,3 ', 4,4' -benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4' -diphenyl sulfide tetracarboxylic dianhydride, 3,3 ', 4,4' -diphenyl sulfone tetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, 2,2-bis [4- (3,4-dicarboxyphenoxy) phenyl ] hexafluoropropane dianhydride, 1, 4-bis (3,4-dicarboxyphenoxy) -2,2 ', 3-trimethylbenzene dianhydride, 1, 4-bis (3,4-dicarboxyphenoxy) -2,3 ' -di-tert-butyl-benzene dianhydride, 4' -dimethyl (3, 4' -dimethyl-phenyl) -1, 3 ' -dimethyl (3, 4' -dimethyl-3 ' -methyl-phenyl) dianhydride, and 1, 4' -dimethyl-3 ' -dimethyl-phenyl dianhydride.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609712A (en) * | 1984-06-18 | 1986-09-02 | General Electric Company | Method for preparing monomeric and polymeric bis(dicarboxyphenyl) sulfone compounds |
| CN101265328A (en) * | 2008-04-23 | 2008-09-17 | 东华大学 | Method for preparing negative photosensitive polyimide based on 2,2-di[4-(2,4-diaminophenyloxy)phenyl]hexafluoropropane |
| CN102976983A (en) * | 2012-10-25 | 2013-03-20 | 华中科技大学 | Sulfonyl fluorine-containing diamine compound and polyimide film material, and preparation method thereof |
| CN104387586A (en) * | 2014-11-11 | 2015-03-04 | 桂林理工大学 | Soluble transparent fluorine-containing polyimide material and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609712A (en) * | 1984-06-18 | 1986-09-02 | General Electric Company | Method for preparing monomeric and polymeric bis(dicarboxyphenyl) sulfone compounds |
| CN101265328A (en) * | 2008-04-23 | 2008-09-17 | 东华大学 | Method for preparing negative photosensitive polyimide based on 2,2-di[4-(2,4-diaminophenyloxy)phenyl]hexafluoropropane |
| CN102976983A (en) * | 2012-10-25 | 2013-03-20 | 华中科技大学 | Sulfonyl fluorine-containing diamine compound and polyimide film material, and preparation method thereof |
| CN104387586A (en) * | 2014-11-11 | 2015-03-04 | 桂林理工大学 | Soluble transparent fluorine-containing polyimide material and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| "新型功能性聚酰亚胺的合成与性能研究";黄孝华;《中国优秀博士学位论文全文数据库，工程科技I辑》;20120715;第2.2-2.4部分 * |
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