CN106496557A - A kind of preparation method of high transparency high temperature resistant fluorinated polyimide resin - Google Patents
A kind of preparation method of high transparency high temperature resistant fluorinated polyimide resin Download PDFInfo
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- CN106496557A CN106496557A CN201610940374.0A CN201610940374A CN106496557A CN 106496557 A CN106496557 A CN 106496557A CN 201610940374 A CN201610940374 A CN 201610940374A CN 106496557 A CN106496557 A CN 106496557A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
A kind of preparation method of high transparency high temperature resistant fluorinated polyimide resin, it is related to a kind of preparation method of polyimide resin, the hyperbranched fluoro polyimide material that the present invention is prepared, the introducing of linear segment can increase the chain entanglement of polymer, in addition, the introducing of side chain can increase the dissolubility of polymer, further reduce polymeric birefringent value, obtain ridge waveguide bar with cross-linking type dissaving polymer using ion etching.Successfully synthesize a series of fluorine-containing super-branched polyimide materials with different lineal measures using two steps chemistry clasp method.Prepared super-branched polyimide has excellent heat stability, has good dissolubility in organic solvent.The mechanics of material, calorifics, optical property have linear according to several relations well with the content of Triamine monomer in material.Ridge waveguide bar is successfully prepared, and has excellent optical property, improve its mechanical performance.
Description
Technical field
The present invention relates to a kind of preparation method of high transparency high temperature resistant fluorinated polyimide resin, more particularly to a kind of high
The preparation method of transparent high temperature resistant fluorinated polyimide resin.
Background technology
Polyimides containing trifluoromethyl were just had been reported that early in 1967, and in fluorinated polyimide most study polymerization
Thing.It is 6FDA to obtain most common dianhydride used in fluorinated polyimide, and it is by formula by o-Dimethylbenzene with Hexafluoro acetone
Figure 1.10 is synthesized.
.
Although there is prominent performance and many potential using values by the polyimides that 6FDA synthesizes, due to 6FDA
With high costs, make the application of this kind of polymer receive very big restriction.It show which as shown in Figure 3 with the polymer of APB synthesis.
Belong to such dianhydride and also have FPhDA, FBDA, 3FCDA, 6FCDA, 6FBPDA etc..Auman etc. gathers to reduce 6FDA
The higher CTE of acid imide, designs and has synthesized 6FCDA and 3FCDA, this be using in molecule three and ring improving macromolecular chain
Rigidity.The polyimides obtained by 6FCDA and 3FCDA have higher intensity and modulus, and more surprising also having is higher
Elongation at break.The CTE of 6FCDA/6FBA and 6FCDA/ODA is lower than the CTE of 6FDA/6FBA and 6FDA/ODA, and correspondingly,
The former TgThen significantly high than the latter, illustrate three and the rigid chain of phenyl ring is conducive to reduction and the T of CTE reallygRaising.
(Figure 5.)
The common diamidogen containing trifluoromethyl or hexafluoro propyl group has 6FBA, 3,5-BDTF, BDTF etc..
Content of the invention
It is an object of the invention to provide a kind of preparation method of high transparency high temperature resistant fluorinated polyimide resin, the present invention
The hyperbranched fluoro polyimide material for preparing, the introducing of linear segment can increase the chain entanglement of polymer, improve its machine
Tool performance.Additionally, the introducing of side chain can increase the dissolubility of polymer, prepared super-branched polyimide has excellent
Heat stability, has good dissolubility in organic solvent.The mechanics of material, calorifics, optical property and triamine list in material
The content of body has linear according to several relations well.
The purpose of the present invention is achieved through the following technical solutions：
A kind of preparation method of high transparency high temperature resistant fluorinated polyimide resin, the present invention are existed with trimellitic anhydride by 6FAPB
Chemical clasp method synthesizes a series of fluorine-containing super-branched polyimide materials, and methods described includes following technological process：
A kind of preparation method of described high transparency high temperature resistant fluorinated polyimide resin, its preparation process described are as follows：
（1）To in reaction vessel there-necked flask add 3 '-（Trifluoromethyl）- [1,1 '-phenylbenzene] -2,5- glycol（Dry）（3’-
Methyl-[1,1 '-phenylbenzene] -2,5- glycol）5- nitros-benzotrifluoride chloro- with 2-, and solvent DMF is added with band water medicine first
Benzene, makees catalyst with potassium carbonate and washes the powder for obtaining, dries；
（2）Primary product 2,5- is double（4-nitro-2 -（Trifluoromethyl）Phenoxy group）- 3 -（Trifluoromethyl）-
1,1'- biphenyl is put in three-neck flask, adds iron powder and ethanol, water reaction, is stirred to having powder, drying；
（3）Product ethyl alcohol recrystallization after reduction, takes crystal drying；
（4）A series of hyperbranched fluoro polyimide material of linear/A2+B3 copolymerization of synthesis, the introducing of linear segment can increase
The chain entanglement of addition polymerization compound, improves its mechanical performance；Ridge ripple obtained using ion etching with cross-linking type dissaving polymer
Sliver；Successfully synthesize a series of fluorine-containing super-branched polyimide materials with different lineal measures using two steps chemistry clasp method
Material.
A kind of preparation method of described high transparency high temperature resistant fluorinated polyimide resin, the step（1) in, 3 '（Three
Methyl fluoride）- [1,1 '-phenylbenzene] -2,5- glycol (is dried）（3 '-methyl-[1,1 '-phenylbenzene] -2,5- glycol）5- chloro- with 2-
The mol ratio of nitro-benzotrifluoride is preferably 0.1:0.2, potassium carbonate quality：138 × 1.5 × 0.1=21g, DMF volume：（25.5
+47）The chloro- 5- nitros of × 3.5=200mL wherein 2--benzotrifluoride excessive 5%.
A kind of preparation method of described high transparency high temperature resistant fluorinated polyimide resin, the step（3) in, addition
6FAPB is 2.5850 with trimellitic anhydride mass ratio：2.1134, wherein trimellitic anhydride quality：192.13×2×1.1×0.5
×0.01=2.1134g.
Advantages of the present invention with effect is：
The hyperbranched fluoro polyimide material that the present invention is prepared, the introducing of linear segment can increase the chain of polymer and twine
Knot, improves its mechanical performance.Additionally, the introducing of side chain can increase the dissolubility of polymer, further reduce polymer two-fold
Value, and the calorifics to material is penetrated, and mechanics, optical property are studied, and ion etching are adopted with cross-linking type dissaving polymer
Obtain ridge waveguide bar.Successfully synthesize a series of fluorine-containing over-expenses with different lineal measures using two steps chemistry clasp method
Change polyimide material.Prepared super-branched polyimide has excellent heat stability, has in organic solvent very well
Dissolubility.The mechanics of material, calorifics, optical property have linear according to number pass well with the content of Triamine monomer in material
System.Alkynyl end-blocking being carried out to one of which polymer successfully, and having obtained calorifics, the more excellent cross-linking type of optical property contains
Fluorine super-branched polyimide material.Device preparation is carried out using crosslinked polyimide E-co FHBPI 50, ridge is successfully prepared
Type waveguide bar, and have excellent optical property.
Description of the drawings
Fig. 1 is one of fluoropolymer product result schematic diagram；
Two schematic diagrams of the Fig. 2 for fluoropolymer product result；
Fig. 3 is the polymer schematic diagram that this kind of polymer of 6FDA is synthesized with APB in background technology.
Specific embodiment
With reference to embodiment, the present invention is described in detail.
Embodiment
One kind uses 3 '-（Trifluoromethyl）- [1,1 '-phenylbenzene] -2,5- glycol and 3 '-methyl-[1,1 '-phenylbenzene] -2,
The method that 5- glycol prepares the resistant to elevated temperatures polyimides of high transparency by a series of chemical reaction, its preparation process are as follows：
（1）To in reaction vessel there-necked flask add 3 '-（Trifluoromethyl）- [1,1 '-phenylbenzene] -2,5- glycol（Dry）（3’-
Methyl-[1,1 '-phenylbenzene] -2,5- glycol）5- nitros-benzotrifluoride chloro- with 2-, and solvent DMF is added with band water medicine first
Benzene（80mL), catalyst is made with potassium carbonate and react 4 hours under conditions of 135 140 DEG C, then rise high-temperature to 150
DEG C reaction 4 hours.Nitrogen is continually fed in course of reaction, and is stirred.Discharge in mixture of ice and water, by the powder water for obtaining
It is washed till solution colourless, again with methanol is washed 23 times, is put in vacuum drying oven and dries.
（2）Primary product 2,5- is double（4-nitro-2 -（Trifluoromethyl）Phenoxy group）- 3 -（Fluoroform
Base）- 1,1'- biphenyl is put in three-neck flask, adds iron powder and ethanol：Water 60：30mL, is initially charged ethanol in Dropping funnel：
Water 15：15mL hydrochloric acid solution 3.52mL start Deca 3-4 drop, are then slowly added dropwise 2 hours, and complete rear reaction 4 in 2 hours is little
When.So
The sodium hydroxide and ethanol of 1.68g are added in Dropping funnel afterwards：Water 15：The solution of 15mL, half an hour will be burnt to three
Drip in bottle.Reaction temperature in course of reaction is controlled at 80 100 DEG C.After question response terminates, by the heat for heating in advance
Ethanol pours hot sucking filtration on the filter paper of hourglass.Solution after by sucking filtration is poured in mixture of ice and water, is stirred to there is powder.Sucking filtration
Washing is repeatedly washed to colourless methanol, is then placed in 50 DEG C of drying in baking oven.（Nitro is reduced into amino.）
（3）Product ethyl alcohol recrystallization after reduction, takes crystal drying.Use product（6FAPB）With trimellitic anhydride（Cross
Amount）It is put in reaction vessel, adds glacial acetic acid（14mL) and DMAc, 10 hours of firm boiling reaction are heated to.10 hours afterwards
Stopped reaction, stands a night, treats second day to discharge, then washes material.In this reaction, because having used chemical clasp method to cause synthesis length
The dianhydride monomer of segment.
（4）In order to solve super-branched polyimide chain entanglement this problem weaker, a series of dianhydride of long-chain-segments is prepared
Monomer, and a series of fluorine-containing super-branched polyimide materials are synthesized by two steps chemistry clasp method with Triamine monomer, and right
Its mechanics, calorifics, optical property are inquired into.Attempt the making that fiber waveguide device is carried out with the material of synthesis.In addition, synthesize one
The hyperbranched fluoro polyimide material of array of linear/A2+B3 copolymerization, the introducing of linear segment can increase the chain of polymer and twine
Knot, improves its mechanical performance.In addition, the introducing of side chain can increase the dissolubility of polymer, further reduce polymer two-fold
Penetrate value, and our calorifics to material, mechanics, optical property are studied.
Dissolve each other problem to solve sandwich layer covering of the waveguide material in processing and making process, introducing crosslinked group, crosslinking
The heat stability and solvent resistance of film is enhanced, and optical birefringence value decreases.Then overspend with cross-linking type
Fluidized polymer obtains ridge waveguide bar using ion etching.Successfully synthesized using two steps chemistry clasp method a series of with not
The fluorine-containing super-branched polyimide material of synteny length.
Prepared super-branched polyimide has excellent heat stability, has dissolving well in organic solvent
Property.
The mechanics of material, calorifics, optical property have linear according to several relations well with the content of Triamine monomer in material.
Alkynyl end-blocking is carried out to one of which polymer successfully, and has obtained calorifics, the more excellent cross-linking type fluorine-containing of optical property
Super-branched polyimide material.Device preparation is carried out using crosslinked polyimide E-coFHBPI 50, ridge is successfully prepared
Waveguide bar, and have excellent optical property.Three kinds of dianhydride monomers containing different side bases of synthesis（Such as trifluoromethyl, first
Base ...）, and the polyetherimide containing different side bases is prepared by the chemistry clasp method polymerization of two steps from a series of diamidogen
Amine material, and to its structure, mechanics, calorifics, optics are studied in detail.Successful design and synthesize containing different side bases
Diether type dianhydride monomer, and its structure is characterized to which by infrared, nuclear-magnetism, mass spectrum, DSC etc..Contained using three kinds synthesized
The dianhydride monomer for having different side bases is polymerized with the diamine monomer of three kinds of ether-containing keys, using two steps chemistry clasp method, is synthesized
Three serial linear polyether acid imide materials.By infrared, elementary analysiss, nuclear-magnetism is tested, it was demonstrated that its structure with designed
Polymer is consistent.
Molecular weight to polymer, viscosity are characterized, it was demonstrated that polymer has larger molecular weight.To its three polymer
Aggregated structure, mechanics, thermal property are tested.Prepared polymeric film has good mechanical property, and modulus is big
In 2GPa；Polymer has higher glass transition temperature, is above 200oC；Polymer has a preferable heat stability, and 5
% thermal weight loss temperature is above 520oC；Polymer has excellent dissolubility, in common solvent such as DMAC, DMSO, in DMF
Room temperature is solvable.There is the polyimide film color for preparing shallower, which terminates wavelength all in 380 below nm, and shows height
Degree permeability (at 800 nm, transmitance is 87-89 %)；The refractive index of synthesized polymer between 1.5764-1.5970,
The birefringence value of polymer is in 0.0122-0.0175.Fluoro-containing copolymer film communication band (1310 nm, 1550 nm) have compared with
Little absorption.Product result is as shown in the figure.
Claims (4)
1. a kind of preparation method of high transparency high temperature resistant fluorinated polyimide resin, it is characterised in that the present invention be by 6FAPB with
Trimellitic anhydride synthesizes a series of fluorine-containing super-branched polyimide materials in chemical clasp method, and methods described includes following technique stream
Journey：
.
2. the preparation method of a kind of high transparency high temperature resistant fluorinated polyimide resin according to claim 1, its feature exist
In its preparation process described is as follows：
（1）To in reaction vessel there-necked flask add 3 '-（Trifluoromethyl）- [1,1 '-phenylbenzene] -2,5- glycol（Dry）（3’-
Methyl-[1,1 '-phenylbenzene] -2,5- glycol）5- nitros-benzotrifluoride chloro- with 2-, and solvent DMF is added with band water medicine first
Benzene, makees catalyst with potassium carbonate and washes the powder for obtaining, dries；
（2）Primary product 2,5- is double（4-nitro-2 -（Trifluoromethyl）Phenoxy group）- 3 -（Trifluoromethyl）-
1,1'- biphenyl is put in three-neck flask, adds iron powder and ethanol, water reaction, is stirred to having powder, drying；
（3）Product ethyl alcohol recrystallization after reduction, takes crystal drying；
（4）A series of hyperbranched fluoro polyimide material of linear/A2+B3 copolymerization of synthesis, the introducing of linear segment can increase
The chain entanglement of addition polymerization compound, improves its mechanical performance；Ridge ripple obtained using ion etching with cross-linking type dissaving polymer
Sliver；Successfully synthesize a series of fluorine-containing super-branched polyimide materials with different lineal measures using two steps chemistry clasp method
Material.
3. the preparation method of a kind of high transparency high temperature resistant fluorinated polyimide resin according to claim 1, its feature exist
In the step（1) in, 3 '（Trifluoromethyl）- [1,1 '-phenylbenzene] -2,5- glycol (is dried）（3 '-methyl-[1,1 '-di-
Benzene] -2,5- glycol）The mol ratio of 5- nitros-benzotrifluoride chloro- with 2- is preferably 0.1:0.2, potassium carbonate quality：138×1.5
× 0.1=21g, DMF volume：（25.5+47）The chloro- 5- nitros of × 3.5=200mL wherein 2--benzotrifluoride excessive 5%.
4. the preparation method of a kind of high transparency high temperature resistant fluorinated polyimide resin according to claim 1, its feature exist
In the step（3), in, the 6FAPB of addition is 2.5850 with trimellitic anhydride mass ratio：2.1134, wherein trimellitic anhydride
Quality：192.13×2×1.1×0.5×0.01=2.1134g.
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| CN110894294A (en) * | 2019-12-09 | 2020-03-20 | 中国科学院长春应用化学研究所 | High-temperature-resistant fluorine-containing polyimide heat-shrinkable tube and preparation method thereof |
| CN112708130A (en) * | 2019-10-24 | 2021-04-27 | 中国石油化工股份有限公司 | Colorless transparent polyimide film and preparation method thereof |
| CN114133565A (en) * | 2021-12-08 | 2022-03-04 | 江苏艾森半导体材料股份有限公司 | Hyperbranched polyimide resin and preparation method and application thereof |
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| CN114133565A (en) * | 2021-12-08 | 2022-03-04 | 江苏艾森半导体材料股份有限公司 | Hyperbranched polyimide resin and preparation method and application thereof |
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