CN103497336A - Soluble polyimide with tertiary butyl and non-coplanar structure and preparation method thereof - Google Patents
Soluble polyimide with tertiary butyl and non-coplanar structure and preparation method thereof Download PDFInfo
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- CN103497336A CN103497336A CN201310478144.3A CN201310478144A CN103497336A CN 103497336 A CN103497336 A CN 103497336A CN 201310478144 A CN201310478144 A CN 201310478144A CN 103497336 A CN103497336 A CN 103497336A
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Abstract
The invention discloses soluble polyimide with tertiary butyl and non-coplanar structure and a preparation method thereof. The soluble polyimide with tertiary butyl and non-coplanar structure has a structural formula shown as follow. Ar is an aromatic structure. Under the protection of nitrogen, aromatic diamine monomer and aromatic dianhydride both having the tertiary butyl and non-coplanar structure are used as raw materials; the soluble polyimide with tertiary butyl and non-coplanar structure with excellent comprehensive performances is prepared by high-temperature solution polycondensation. The preparation method is simple in process and low in cost, has no special requirements on reaction equipment, and is applicable to industrial production; the prepared soluble polyimide has good solubility, superior heat resistance stability and excellent optical property.
Description
Technical field
The invention belongs to technical field of polymer materials, particularly a kind of containing the tertiary butyl and non-coplanar structure soluble polyimide and preparation method thereof.
Background technology
Polyimide is the aromatic heterocyclic polymer that a class contains imide ring on the molecular structure main chain, overall characteristic with high-low temperature resistant, radiation hardness, chemical stability excellence, dielectric properties and good mechanical performance, over nearly 40 years, in many high-tech areas, be widely applied, as aerospace, microelectronics, photoelectron and automotive industry etc.Yet, due to molecule chain rigidity and intermolecular strong interaction, make common polyimide material present the shortcomings such as neither melting is not dissolved yet, poor processability, thereby further limited their widespread use.In addition, height conjugacy and charge transfer complex effect (CTC) due to the polyimide molecule structure, material presents color in various degree usually, and in visible-range, the transparency is poor, makes them be very restricted equally in the application of optical field.In order to solve above-mentioned shortcoming, prepare that solubility property is good, optical transparence is high and the polyimide material of the excellent combination property such as good thermal stability, researcher has carried out a large amount of research in this respect.
Fluorine-containing solubility polyethers imide correlative study achievement has many reports in recent years, CN102898644, CN1434024, the patents such as CN101246222 have been reported the research of fluorine-containing soluble polyimide in succession, then this class material is owing to having introduced more flexible ehter bond in molecular backbone chain, often make the resistance to elevated temperatures of this class material have substantial degradation than the standard polyimide, its second-order transition temperature is mostly below 260 ℃, in modern microelectronics and photoelectron industry, require Kapton at least can bear the hot processing temperature more than 260 ℃, thereby limited to a certain extent their application.Adopt synthetic have large space steric hindrance and non-coplanar structure soluble polyimide material, it is also the focus of Recent study, by destroying upright and outspoken chain structure and the intermolecular interaction force of main chain, destroy the formation of polyimide molecule structure charge transfer Complexes (CTC), improved greatly solubility property and the optical clear performance of polyimide.Synthetic simple, the advantages such as price is cheap, material excellent combination property of this method are generally to adopt one of method of synthesizing soluble polyimide at present.Understand a kind of preparation method (CN1919829) of alkyl substituent aromatic diamine such as human hairs such as Yu Xinhai; Yellow the people such as defends and has studied soluble polyimide material containing tert-butyl and preparation method thereof (CN1316449); The people such as Zhang Yi have reported a kind of soluble functional polyimide containing carbazole structure and its preparation method and application (CN102757560).Materials has good thermal characteristics, excellent solubility property, the high over-all propertieies such as optical transparence, low-k and low rate of moisture absorption, in fields such as aerospace, microelectronics and photoelectrons, is widely used.
Summary of the invention
The purpose of this invention is to provide a kind of containing the tertiary butyl and non-coplanar structure soluble polyimide and preparation method thereof.
Thinking of the present invention: under nitrogen protection; aromatic diamine monomers and the aromatic dianhydride monomer that contains the tertiary butyl and non-coplanar structure of take is raw material; by high temperature solution polycondensation react prepare excellent combination property containing the tertiary butyl and non-coplanar structure soluble polyimide, wherein the preparation method containing the aromatic diamine monomers of the tertiary butyl and non-coplanar structure is documented in (application number: 2013104485149) in the previous patent application of contriver
General structure containing the tertiary butyl and non-coplanar structure soluble polyimide of the present invention is:
Wherein Ar is a kind of in following 11 kinds of aromatic structures:
The above-mentioned preparation method containing the tertiary butyl and non-coplanar structure soluble polyimide is:
(1) under nitrogen protection; to wait mole containing the tertiary butyl and non-coplanar structure aromatic diamine monomers and aromatic dianhydride monomer and stir and be dissolved in organic solvent under room temperature; making its total solid content mass percent is 5 ~ 15%; add catalyzer isoquinoline 99.9; 100 ~ 120 ℃ of reactions 6 ~ 12 hours; be warming up to 180 ~ 220 ℃ and continue reaction 12 ~ 20 hours, make the brown color viscous solution.
(2) after being cooled to room temperature, dilutes with chloroform brown color viscous solution step (1) made, with precipitation agent, precipitated again, then pass through successively filtration, drying, be N with DMF, the N'-dimethyl formamide dissolves again, redeposition, refilter and dry again, finally makes fibrous polyimide.
Described is 3,3 ˊ-di-t-butyl-4,4 ˊ-diamino-phenyl-4 〞-4-tert-butyltoluene containing the tertiary butyl and non-coplanar structure aromatic diamines, and its structural formula is:
Described aromatic dianhydride is 3, 3 ˊ, 4, 4 ˊ-pyromellitic acid anhydride, 3, 3 ˊ, 4, 4 ˊ-bibenzene tetracarboxylic dianhydride, 3, 3 ˊ, 4, 4 ˊ-diphenyl ether tetraformic dianhydride, 3, 3 ˊ, 4, 4 ˊ-benzophenone tetracarboxylic dianhydride, 3, 3 ˊ, 4, 4 ˊ-diphenyl thio-ether tetrformate dianhydride, 3, 3 ˊ, 4, 4 ˊ-diphenyl sulfone tetraformic acid dianhydride, 2, 2-two (3, 4-dicarboxyl phenyl) hexafluoropropane dianhydride, 2, 2-is two, and [4-(3, the 4-di carboxyl phenyloxy) phenyl] hexafluoropropane dianhydride, 1, 4-two (3, the 4-di carboxyl phenyloxy)-2, 3 ˊ-di-t-butyl benzene dianhydride, 3, 3 ˊ-bis-(3, the 4-di carboxyl phenyloxy) phenyl ether dianhydride and 1, 6-two (3, the 4-di carboxyl phenyloxy) a kind of in-naphthalene dianhydride.
Described organic solvent is meta-cresol or para-chlorophenol.
The consumption of described catalyzer is 0.5 ~ 2.5% of the quality that always feeds intake.
Described precipitation agent is methyl alcohol or ethanol.
The present invention has the following advantages:
(1) polyimide of the present invention has the good solubility energy, not only dissolves in conventional high boiling organic solvent, and wherein partial polymer can also be dissolved in low boiling point solvent, as tetrahydrofuran (THF) (THF), trichloromethane (CHCl
3) and acetone etc., the solubilized characteristic of polymkeric substance in low boiling point solvent, can realize material at low temperature film-forming technique, thereby make material be used widely at microelectronic.
(2) polyimide of the present invention has excellent optical property, and the cutoff wavelength scope is 330 ~ 350 nanometers, wavelength 400 ~ 450 nanometers that transmitance is 80%, and materials is expected to be applied at the microlens optical field.
(3) polyimide of the present invention has superior heat-resistant stability, second-order transition temperature (
t g) more than 280 ℃, the thermolysis starting temperature (
t d) scope is more than 480 ℃, carbon yield is all more than 50%; The high-temperature stability of material, be expected to realize that material is applied as high temperature material.
(4) technological operation of the inventive method is simple, with low cost, simultaneously to conversion unit without particular requirement, be applicable to suitability for industrialized production.
The accompanying drawing explanation
Fig. 1 is the general structure containing the tertiary butyl and non-coplanar structure soluble polyimide of the present invention.
The structural formula containing the tertiary butyl and non-coplanar structure soluble polyimide that Fig. 2 is the embodiment of the present invention 1 preparation.
The structural formula containing the tertiary butyl and non-coplanar structure soluble polyimide that Fig. 3 is the embodiment of the present invention 2 preparations.
The structural formula containing the tertiary butyl and non-coplanar structure soluble polyimide that Fig. 4 is the embodiment of the present invention 3 preparations.
The structural formula containing the tertiary butyl and non-coplanar structure soluble polyimide that Fig. 5 is the embodiment of the present invention 4 preparations.
The structural formula containing the tertiary butyl and non-coplanar structure soluble polyimide that Fig. 6 is the embodiment of the present invention 5 preparations.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention, should understand, these embodiment only are not used in and limit the scope of the invention for the present invention is described, should understand in addition, after the content of having read the present invention's instruction, those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the appended claims limited range of the application equally.
embodiment 1:
(1) under nitrogen protection, by 1.0000 grams (2.2590 mmole) 3,3 ˊ-di-t-butyl-4,4 ˊ-diamino-phenyl-4 〞-4-tert-butyltoluene and 0.4927 gram (2.2590 mmole) 3,3 ˊ, 4,4 ˊ-pyromellitic acid anhydride joins in 13.43 gram meta-cresols, and be warming up to 100 ℃ of reactions 12 hours after adding 0.2238 gram catalyzer isoquinoline 99.9, the system that is stirred under room temperature to be transparence; Be warming up to again 200 ℃ of reactions 12 hours, obtain the brown color viscous liquid.
(2) after being cooled to room temperature, dilutes with chloroform brown color viscous solution step (1) made, with ethanol, precipitated again, then pass through successively filtration, drying, be N with DMF, the N'-dimethyl formamide dissolves again, with the ethanol redeposition, refilter and dry again, finally make faint yellow fibrous polyimide, its structural formula is shown in Figure of description.
embodiment 2:
(1) under nitrogen protection, by 1.0000 grams (2.2590 mmole) 3,3 ˊ-di-t-butyl-4,4 ˊ-diamino-phenyl-4 〞-4-tert-butyltoluene and 0.6646 gram (2.2590 mmole) 3,3 ˊ, 4,4 ˊ-bibenzene tetracarboxylic dianhydride joins in 14.98 gram meta-cresols, and be warming up to 120 ℃ of reactions 6 hours after adding 0.2497 gram catalyzer isoquinoline 99.9, the system that is stirred under room temperature to be transparence; Be warming up to again 180 ℃ of reactions 20 hours, obtain the brown color viscous liquid.
(2) after being cooled to room temperature, dilutes with chloroform brown color viscous solution step (1) made, with ethanol, precipitated again, then pass through successively filtration, drying, be N with DMF, the N'-dimethyl formamide dissolves again, with the ethanol redeposition, refilter and dry again, finally make faint yellow fibrous polyimide, its structural formula is shown in Figure of description.
embodiment 3:
(1) under nitrogen protection, by 1.0000 grams (2.2590 mmole) 3,3 ˊ-di-t-butyl-4,4 ˊ-diamino-phenyl-4 〞-4-tert-butyltoluene and 0.7279 gram (2.2590 mmole) 3,3 ˊ, 4,4 ˊ-benzophenone tetracarboxylic dianhydride joins in 15.55 gram meta-cresols, and be warming up to 110 ℃ of reactions 9 hours after adding 0.2592 gram catalyzer isoquinoline 99.9, the system that is stirred under room temperature to be transparence; Be warming up to again 190 ℃ of reactions 16 hours, obtain the brown color viscous liquid.
(2) after being cooled to room temperature, dilutes with chloroform brown color viscous solution step (1) made, with methyl alcohol, precipitated again, then pass through successively filtration, drying, be N with DMF, the N'-dimethyl formamide dissolves again, with the methyl alcohol redeposition, refilter and dry again, finally make faint yellow fibrous polyimide, its structural formula is shown in Figure of description.
embodiment 4:
(1) under nitrogen protection, by 1.0000 grams (2.2590 mmole) 3,3 ˊ-di-t-butyl-4,4 ˊ-diamino-phenyl-4 〞-4-tert-butyltoluene and 0.7008 gram (2.2590 mmole) 3,3 ˊ, 4,4 ˊ-diphenyl ether tetraformic dianhydride joins in 15.31 gram meta-cresols, and be warming up to 110 ℃ of reactions 9 hours after adding 0.2552 gram catalyzer isoquinoline 99.9, the system that is stirred under room temperature to be transparence; Be warming up to again 200 ℃ of reactions 12 hours, obtain the brown color viscous liquid.
(2) after being cooled to room temperature, dilutes with chloroform brown color viscous solution step (1) made, with methyl alcohol, precipitated again, then pass through successively filtration, drying, be N with DMF, the N'-dimethyl formamide dissolves again, with the methyl alcohol redeposition, refilter and dry again, finally make faint yellow fibrous polyimide, its structural formula is shown in Figure of description.
embodiment 5:
(1) under nitrogen protection, by 1.0000 grams (2.2590 mmole) 3,3 ˊ-di-t-butyl-4,4 ˊ-diamino-phenyl-4 〞-4-tert-butyltoluene and 0. 7597 grams (2.2590 mmole) 2,2-two (3,4-dicarboxyl phenyl) hexafluoropropane dianhydride joins in 15.84 gram para-chlorophenols, and is warming up to 120 ℃ of reactions 6 hours after adding 0.2640 gram catalyzer isoquinoline 99.9, the system that is stirred under room temperature to be transparence; Be warming up to again 190 ℃ of reactions 16 hours, obtain the brown color viscous liquid.
(2) after being cooled to room temperature, dilutes with chloroform brown color viscous solution step (1) made, with methyl alcohol, precipitated again, then pass through successively filtration, drying, be N with DMF, the N'-dimethyl formamide dissolves again, with the methyl alcohol redeposition, refilter and dry again, finally make faint yellow fibrous polyimide, its structural formula is shown in Figure of description.
Claims (2)
1. one kind contains the tertiary butyl and non-coplanar structure soluble polyimide, it is characterized in that the described general structure containing the tertiary butyl and non-coplanar structure soluble polyimide is:
Wherein Ar is a kind of in following 11 kinds of aromatic structures:
2. the preparation method containing the tertiary butyl and non-coplanar structure soluble polyimide according to claim 1 is characterized in that concrete steps are:
(1) under nitrogen protection, to wait mole containing the tertiary butyl and non-coplanar structure aromatic diamine monomers and aromatic dianhydride monomer and stir and be dissolved in organic solvent under room temperature, making its total solid content mass percent is 5 ~ 15%, add catalyzer isoquinoline 99.9,100 ~ 120 ℃ of reactions 6 ~ 12 hours, be warming up to 180 ~ 220 ℃ and continue reaction 12 ~ 20 hours, make the brown color viscous solution;
(2) after being cooled to room temperature, dilutes with chloroform brown color viscous solution step (1) made, with precipitation agent, precipitated again, then pass through successively filtration, drying, be N with DMF, the N'-dimethyl formamide dissolves again, redeposition, refilter and dry again, finally makes fibrous polyimide;
Described is 3,3 ˊ-di-t-butyl-4,4 ˊ-diamino-phenyl-4 〞-4-tert-butyltoluene containing the tertiary butyl and non-coplanar structure aromatic diamines, and its structural formula is:
Described aromatic dianhydride is 3, 3 ˊ, 4, 4 ˊ-pyromellitic acid anhydride, 3, 3 ˊ, 4, 4 ˊ-bibenzene tetracarboxylic dianhydride, 3, 3 ˊ, 4, 4 ˊ-diphenyl ether tetraformic dianhydride, 3, 3 ˊ, 4, 4 ˊ-benzophenone tetracarboxylic dianhydride, 3, 3 ˊ, 4, 4 ˊ-diphenyl thio-ether tetrformate dianhydride, 3, 3 ˊ, 4, 4 ˊ-diphenyl sulfone tetraformic acid dianhydride, 2, 2-two (3, 4-dicarboxyl phenyl) hexafluoropropane dianhydride, 2, 2-is two, and [4-(3, the 4-di carboxyl phenyloxy) phenyl] hexafluoropropane dianhydride, 1, 4-two (3, the 4-di carboxyl phenyloxy)-2, 3 ˊ-di-t-butyl benzene dianhydride, 3, 3 ˊ-bis-(3, the 4-di carboxyl phenyloxy) phenyl ether dianhydride and 1, 6-two (3, the 4-di carboxyl phenyloxy) a kind of in-naphthalene dianhydride,
Described organic solvent is meta-cresol or para-chlorophenol;
The consumption of described catalyzer is 0.5 ~ 2.5% of the quality that always feeds intake;
Described precipitation agent is methyl alcohol or ethanol.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104356387A (en) * | 2014-11-11 | 2015-02-18 | 桂林理工大学 | Soluble polyimide material having non-coplanar structure and preparation method thereof |
| CN104356386A (en) * | 2014-11-11 | 2015-02-18 | 桂林理工大学 | Soluble polyimide containing fluorine and isopropyl structure 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 |
| CN104861162A (en) * | 2015-05-20 | 2015-08-26 | 上海交通大学 | Soluble polyimide with tert-butyl and triphenylamine structure and preparation method of soluble polyimide |
| CN104927054A (en) * | 2015-06-29 | 2015-09-23 | 桂林理工大学 | Soluble polyimide comprising tertiary butyl and morpholinyl structure and preparation method of soluble polyimide |
| CN104987506A (en) * | 2015-06-29 | 2015-10-21 | 桂林理工大学 | Soluble polyimide containing tert-butyl and benzofuran structure and preparation method of soluble polyimide |
| CN105017532A (en) * | 2015-06-29 | 2015-11-04 | 桂林理工大学 | Polyimide containing tertiary butyl and octadecyloxy structures, and preparation method thereof |
| CN108383733A (en) * | 2018-01-15 | 2018-08-10 | 上海交通大学 | Diamine monomer containing tertiary butyl and cycloaliphatic ring and its preparation and application |
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| US20090299014A1 (en) * | 2007-04-11 | 2009-12-03 | Cheil Industries Inc. | 3,4-Dicarboxy-1,2,3,4-tetrahydro-6-t-butyl-1-naphthalene-succinic Dianhydride and Liquid Crystal Aligning Agent Comprising Polyimide Resin Prepared from the Dianhydride |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104356387A (en) * | 2014-11-11 | 2015-02-18 | 桂林理工大学 | Soluble polyimide material having non-coplanar structure and preparation method thereof |
| CN104356386A (en) * | 2014-11-11 | 2015-02-18 | 桂林理工大学 | Soluble polyimide containing fluorine and isopropyl structure 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 |
| CN104861162A (en) * | 2015-05-20 | 2015-08-26 | 上海交通大学 | Soluble polyimide with tert-butyl and triphenylamine structure and preparation method of soluble polyimide |
| CN104927054A (en) * | 2015-06-29 | 2015-09-23 | 桂林理工大学 | Soluble polyimide comprising tertiary butyl and morpholinyl structure and preparation method of soluble polyimide |
| CN104987506A (en) * | 2015-06-29 | 2015-10-21 | 桂林理工大学 | Soluble polyimide containing tert-butyl and benzofuran structure and preparation method of soluble polyimide |
| CN105017532A (en) * | 2015-06-29 | 2015-11-04 | 桂林理工大学 | Polyimide containing tertiary butyl and octadecyloxy structures, and preparation method thereof |
| CN104927054B (en) * | 2015-06-29 | 2017-06-30 | 桂林理工大学 | Soluble polyimide containing the tert-butyl group and morpholine based structures and preparation method thereof |
| CN104987506B (en) * | 2015-06-29 | 2017-12-12 | 桂林理工大学 | Soluble polyimide containing the tert-butyl group and benzofuran structure and preparation method thereof |
| CN108383733A (en) * | 2018-01-15 | 2018-08-10 | 上海交通大学 | Diamine monomer containing tertiary butyl and cycloaliphatic ring and its preparation and application |
| CN108383733B (en) * | 2018-01-15 | 2020-11-24 | 上海交通大学 | Diamine monomer containing tertiary butyl and aliphatic ring, preparation and application thereof |
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