CN110511379A - A kind of preparation method and product of functionalization graphene polyimide film - Google Patents
A kind of preparation method and product of functionalization graphene polyimide film Download PDFInfo
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- 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
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
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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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C08K3/00—Use of inorganic substances as compounding ingredients
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Abstract
The invention discloses the preparation methods and product of a kind of functionalization graphene polyimide film.First by diamines and dianhydride synthesis of polyimides resin, modified graphene is then added, is made by imidization.The present invention is added modified graphene, increases the degree of scatter of graphene in the material, significantly increase the heating conduction and mechanical property of material, to meet the needs in market in the preparation process of Kapton.
Description
Technical field
The invention belongs to polyimides technical fields, and in particular to a kind of functionalization graphene polyimide film
Preparation method and product.
Background technique
Polyimides refers to the quasi polymer for containing imide ring (- CO-NH-CO-) on main chain, wherein to contain phthaloyl
The polymer of imine structure is mostly important.Polyimides as a kind of special engineered material, have been widely used Aeronautics and Astronautics,
The fields such as microelectronics, nanometer, liquid crystal, seperation film, laser.Polyimide high temperature-resistant is up to 400 DEG C or more, long-term use temperature model
- 200~300 DEG C are enclosed, partially without sharp melting point, high insulating property, dielectric loss only 0.004~0.007.
Graphene is a kind of Two-dimensional Carbon nanometer material for forming hexangle type in honeycomb lattice with sp2 hybridized orbit by carbon atom
Material.Graphene carbon atom has 4 valence electrons, wherein 3 are electronically generated sp key, i.e., each carbon atom contributes one to be located at pz rail
Non- bonding electrons on road, the pz track and plane of neighbour's atom can form pi bond at vertical direction, and the pi bond newly formed is in partly to fill out
Full state.Research confirms that the ligancy of carbon atom is 3 in graphene, and the bond distance between every two adjacent carbon atom is 1.42 × 10
Rice, the angle between key and key is 120 °.Other than σ key and other carbon atom chains are connected into the cellular layer structure of hexagonal ring,
The pz track perpendicular to layer plane of each carbon atom can form polyatomic big pi bond through holostrome, thus have excellent
Conduction and optical property.
Graphene is one of highest material of known strength, while also having good toughness, and can be bent, graphene
Theoretical Young's modulus reach 1.0TPa, intrinsic tensile strength be 130GPa.Possessed very by the graphite paper that graphene platelet forms
More holes, thus graphite paper seems very crisp, however, obtaining functionalization graphene through oxidation, then is made into stone by functionalization graphene
Black paper then can be abnormal firm tough.Graphene has extraordinary heat-conductive characteristic.Pure flawless single-layer graphene is led
Hot coefficient is up to 5300W/mK, is the highest carbon material of thermal coefficient so far, receives higher than single-walled carbon nanotube and multi wall carbon
Mitron.When it is as carrier, thermal coefficient is also up to 600W/mK.In addition, the trajectory thermal conductivity of graphene can make unit circle
The lower limit of the trajectory thermal conductivity of the carbon nanotube of week and length moves down.
Although graphene has good performance, still, be difficult to evenly dispersed, needed to graphene in polyimide material
Modification could utilize its excellent properties well.
Summary of the invention
The purpose of the present invention is to provide the preparation methods and its system of a kind of functionalization graphene polyimide film
Product.
A kind of preparation method of functionalization graphene polyimide film carries out in accordance with the following steps:
(1) at room temperature, diamines and dianhydride are added to reaction kettle, organic solvent is added under nitrogen protection, stirs evenly
Afterwards, isoquinolin is added, is warming up to 180-200 DEG C, reacts 10-14 hours, reaction solution is poured into ethyl alcohol after cooling and is precipitated, is made poly-
Imide resin；
(2) polyimide resin of synthesis and the agitated reaction kettle of modified graphene are stirred, mixing speed 1500-
2000rpm, mixing time 1-3h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, added by winder and cutting machine
Finished product is made in work.
The diamines is m-phenylene diamine (MPD), 2,2 '-bis- (trifluoromethyl) -4,4 '-benzidines, diphenyldiamine, to benzene
Two ether diamine of diphenol, one of two ether diamine of bisphenol-A or more than one.
The dianhydride be benzophenone dianhydride, biphenyl dianhydride, diphenyl ether dianhydride, hydroquinone di ether dianhydride, 5,5 '-(1,1,
3,3- tetramethyls-disiloxane) carbic anhydride, 1,1,3,3- tetramethyl disiloxane-bis- benzoic acid dianhydride, isophthalic two
One of two ether dianhydride of phenol or more than one.
The organic solvent is metacresol, cresols, dimethylformamide, one of N-Methyl pyrrolidone or one kind
More than.
The modified graphene the preparation method is as follows:
(1) graphene is dissolved in 25% ethanol water, adds butyramide, be mixed, obtain graphene dispersion
Liquid；
(2) polyethylene glycol dimethacrylate is added in graphene dispersing solution, is warming up to 40-50 DEG C, mixing is stirred
It mixes；
(3) it is cooled to room temperature, coupling agent and surfactant is added, stirs evenly, is made.
The coupling agent is silane resin acceptor kh-550, Silane coupling reagent KH-570, silane coupling agent KH-602, silane idol
Join agent KH-901, one of silane coupling agent KH-902 or more than one.
The surfactant be neopelex, nonylplenyl ether, neopentyl glycol, sodium nitrilo triacetate,
Triethanolamine, sodium metasilicate, one of polyphosphate or more than one.
The Kapton product that above-mentioned preparation method obtains.
Beneficial effects of the present invention: modified graphene is added in the preparation process of Kapton in the present invention, increases
The degree of scatter of graphene in the material, significantly increases the heating conduction and mechanical property of material, to meet market
It needs.
Specific embodiment
The present invention will be further described combined with specific embodiments below.
Embodiment 1
The preparation of modified graphene:
(1) 100g graphene is dissolved in 300mL25% ethanol water, adds 58g butyramide, be mixed, obtain
To graphene dispersing solution；
(2) 38g polyethylene glycol dimethacrylate is added in graphene dispersing solution, is warming up to 45 DEG C, mixing is stirred
It mixes；
(3) it is cooled to room temperature, 8g silane resin acceptor kh-550 and 5g neopelex is added, stirs evenly, is made
At.
A kind of preparation method of functionalization graphene polyimide film carries out in accordance with the following steps:
(1) at room temperature, m-phenylene diamine (MPD) and benzophenone dianhydride are added to reaction kettle, metacresol are added under nitrogen protection,
After mixing evenly, isoquinolin is added, is warming up to 190 DEG C, reacts 12 hours, reaction solution is poured into ethyl alcohol after cooling and is precipitated, is made
Polyimide resin；
(2) polyimide resin of synthesis and the agitated reaction kettle of modified graphene are stirred, mixing speed 1800rpm,
Mixing time 2h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, added by winder and cutting machine
Finished product is made in work.
Embodiment 2
The preparation of modified graphene:
(1) 120g graphene is dissolved in 280mL25% ethanol water, adds 60g butyramide, be mixed, obtain
To graphene dispersing solution；
(2) 35g polyethylene glycol dimethacrylate is added in graphene dispersing solution, is warming up to 40 DEG C, mixing is stirred
It mixes；
(3) it is cooled to room temperature, 10g Silane coupling reagent KH-570 and 5g nonylplenyl ether is added, stirs evenly, is made.
A kind of preparation method of functionalization graphene polyimide film carries out in accordance with the following steps:
(1) at room temperature, by 2,2 '-bis- (trifluoromethyl) -4,4 '-benzidines are added to biphenyl dianhydride to react
Cresols is added under nitrogen protection in kettle, after mixing evenly, isoquinolin is added, is warming up to 200 DEG C, reacts 10 hours, will be anti-after cooling
It answers liquid to pour into ethyl alcohol precipitation, polyimide resin is made；
(2) polyimide resin of synthesis and the agitated reaction kettle of modified graphene are stirred, mixing speed 1500rpm,
Mixing time 3h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, added by winder and cutting machine
Finished product is made in work.
Embodiment 3
The preparation of modified graphene:
(1) 80g graphene is dissolved in 320mL25% ethanol water, adds 88g butyramide, be mixed, obtain
Graphene dispersing solution；
(2) 28g polyethylene glycol dimethacrylate is added in graphene dispersing solution, is warming up to 50 DEG C, mixing is stirred
It mixes；
(3) it is cooled to room temperature, 12g silane coupling agent KH-602 and 12g neopentyl glycol is added, stirs evenly, is made.
A kind of preparation method of functionalization graphene polyimide film carries out in accordance with the following steps:
(1) at room temperature, by diphenyldiamine and 5,5 '-(1,1,3,3- tetramethyl-disiloxane) carbic acids
Acid anhydride is added to reaction kettle, and dimethylformamide is added under nitrogen protection, after mixing evenly, isoquinolin is added, is warming up to 188 DEG C,
Reaction solution is poured into ethyl alcohol after cooling and is precipitated, polyimide resin is made by reaction 13 hours；
(2) polyimide resin of synthesis and the agitated reaction kettle of modified graphene are stirred, mixing speed 1700rpm,
Mixing time 2.5h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, added by winder and cutting machine
Finished product is made in work.
Embodiment 4
The preparation of modified graphene:
(1) 110g graphene is dissolved in 280mL25% ethanol water, adds 66g butyramide, be mixed, obtain
To graphene dispersing solution；
(2) 35g polyethylene glycol dimethacrylate is added in graphene dispersing solution, is warming up to 42 DEG C, mixing is stirred
It mixes；
(3) it is cooled to room temperature, 8g silane coupling agent KH-901,2g triethanolamine is added, 5g sodium metasilicate stirs evenly, and makes
At.
A kind of preparation method of functionalization graphene polyimide film carries out in accordance with the following steps:
(1) at room temperature, by two ether diamine of bisphenol-A and 1,1,3,3- tetramethyl disiloxane-bis- benzoic acid dianhydride is added
To reaction kettle, N-Methyl pyrrolidone is added under nitrogen protection, after mixing evenly, isoquinolin is added, is warming up to 200 DEG C, reaction
11 hours, reaction solution is poured into ethyl alcohol after cooling and is precipitated, polyimide resin is made；
(2) polyimide resin of synthesis and the agitated reaction kettle of modified graphene are stirred, mixing speed 1900rpm,
Mixing time 2h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, added by winder and cutting machine
Finished product is made in work.
Embodiment 5
The preparation of modified graphene:
(1) 100g graphene is dissolved in 300mL25% ethanol water, adds 58g butyramide, be mixed, obtain
To graphene dispersing solution；
(2) 38g polyethylene glycol dimethacrylate and the poly- isourea of 35g are added in graphene dispersing solution, are warming up to
It 45 DEG C, is mixed；
(3) it is cooled to room temperature, 8g silane resin acceptor kh-550 and 5g neopelex is added, stirs evenly, is made
At.
A kind of preparation method of functionalization graphene polyimide film carries out in accordance with the following steps:
(1) at room temperature, m-phenylene diamine (MPD) and benzophenone dianhydride are added to reaction kettle, metacresol are added under nitrogen protection,
After mixing evenly, isoquinolin is added, is warming up to 190 DEG C, reacts 12 hours, reaction solution is poured into ethyl alcohol after cooling and is precipitated, is made
Polyimide resin；
(2) polyimide resin of synthesis and the agitated reaction kettle of modified graphene are stirred, mixing speed 1800rpm,
Mixing time 2h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, added by winder and cutting machine
Finished product is made in work.
Embodiment 6
The preparation of modified graphene:
(1) 100g graphene is dissolved in 300mL25% ethanol water, adds 58g butyramide, be mixed, obtain
To graphene dispersing solution；
(2) 38g polyethylene glycol dimethacrylate is added in graphene dispersing solution, is warming up to 45 DEG C, mixing is stirred
It mixes；
(3) it is cooled to room temperature, 8g silane resin acceptor kh-550 and 5g neopelex is added, stirs evenly, is made
At.
A kind of preparation method of functionalization graphene polyimide film carries out in accordance with the following steps:
(1) at room temperature, m-phenylene diamine (MPD) and benzophenone dianhydride are added to reaction kettle, metacresol are added under nitrogen protection,
After mixing evenly, isoquinolin is added, is warming up to 190 DEG C, reacts 12 hours, reaction solution is poured into ethyl alcohol after cooling and is precipitated, is made
Polyimide resin；
(2) by the polyimide resin of synthesis, boron cerium aluminium stone and the agitated reaction kettle stirring of modified graphene, mixing speed
1800rpm, mixing time 2h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, added by winder and cutting machine
Finished product is made in work.
Experimental example 1:
According to method as defined in " JB-T2726-1996 Kapton " standard, the polyamides of testing example 1-6 preparation
Imines film tensile strength and thermal coefficient, test result are shown in Table 1:
Table 1
Note: * represents P < 0.05 compared with embodiment 1.
Disclosed above is only specific embodiments of the present invention, and still, the present invention is not limited to this, any this field
What technical staff can think variation should all fall into protection scope of the present invention.
Claims (8)
1. a kind of preparation method of functionalization graphene polyimide film, which is characterized in that carry out in accordance with the following steps:
(1) at room temperature, diamines and dianhydride are added to reaction kettle, organic solvent is added under nitrogen protection, after mixing evenly, adds
Enter isoquinolin, be warming up to 180-200 DEG C, react 10-14 hours, reaction solution is poured into ethyl alcohol after cooling and is precipitated, polyamides Asia is made
Polyimide resin；
(2) polyimide resin of synthesis and the agitated reaction kettle of modified graphene are stirred, mixing speed 1500-2000rpm,
Mixing time 1-3h, is made film liquid；
(3) film liquid is pressed into deaeration kettle, sloughs the bubble in film liquid under vacuum conditions；
(4) film liquid after deaeration casting machine is put into be cast to form Kapton in homogeneous thickness；
(5) Kapton is put into imidization furnace and carries out imidization processing, processed by winder and cutting machine, made
At finished product.
2. the preparation method of functionalization graphene polyimide film according to claim 1, which is characterized in that described
Diamines is m-phenylene diamine (MPD), 2,2 '-bis- (trifluoromethyl) -4,4 '-benzidines, diphenyldiamine, hydroquinone di ether diamines,
One of two ether diamine of bisphenol-A or more than one.
3. the preparation method of functionalization graphene polyimide film according to claim 1, which is characterized in that described
Dianhydride is benzophenone dianhydride, biphenyl dianhydride, diphenyl ether dianhydride, hydroquinone di ether dianhydride, 5,5 '-(1,1,3,3- tetramethyls-two
Siloxanes) carbic anhydride, 1,1,3,3- tetramethyl disiloxane-bis- benzoic acid dianhydride, in two ether dianhydride of resorcinol
One or more.
4. the preparation method of functionalization graphene polyimide film according to claim 1, which is characterized in that described
Organic solvent is metacresol, cresols, dimethylformamide, one of N-Methyl pyrrolidone or more than one.
5. the preparation method of -4 functionalization graphene polyimide films according to claim 1, which is characterized in that institute
State modified graphene the preparation method is as follows:
(1) graphene is dissolved in 25% ethanol water, adds butyramide, be mixed, obtain graphene dispersing solution；
(2) polyethylene glycol dimethacrylate is added in graphene dispersing solution, is warming up to 40-50 DEG C, be mixed；
(3) it is cooled to room temperature, coupling agent and surfactant is added, stirs evenly, is made.
6. the preparation method of functionalization graphene polyimide film according to claim 5, which is characterized in that described
Coupling agent is silane resin acceptor kh-550, Silane coupling reagent KH-570, silane coupling agent KH-602, silane coupling agent KH-901,
One of silane coupling agent KH-902 or more than one.
7. the preparation method of functionalization graphene polyimide film according to claim 5, which is characterized in that described
Surfactant is neopelex, nonylplenyl ether, neopentyl glycol, sodium nitrilo triacetate, triethanolamine, silicic acid
Sodium, one of polyphosphate or more than one.
8. the Kapton product that the preparation method of claim 1-7 obtains.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140121350A1 (en) * | 2012-10-31 | 2014-05-01 | Korea Institute Of Science And Technology | Polyimide-graphene composite material and method for preparing same |
| JP2016127210A (en) * | 2015-01-07 | 2016-07-11 | 株式会社日本触媒 | Carbon material complex composition |
| CN109957126A (en) * | 2019-04-11 | 2019-07-02 | 江苏亚宝绝缘材料股份有限公司 | A kind of preparation method and product of the thermally conductive Kapton of graphene |
-
2019
- 2019-09-04 CN CN201910830463.3A patent/CN110511379A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140121350A1 (en) * | 2012-10-31 | 2014-05-01 | Korea Institute Of Science And Technology | Polyimide-graphene composite material and method for preparing same |
| JP2016127210A (en) * | 2015-01-07 | 2016-07-11 | 株式会社日本触媒 | Carbon material complex composition |
| CN109957126A (en) * | 2019-04-11 | 2019-07-02 | 江苏亚宝绝缘材料股份有限公司 | A kind of preparation method and product of the thermally conductive Kapton of graphene |
Non-Patent Citations (3)
| Title |
|---|
| 周文英等: "《聚合物基导热复合材料》", 30 June 2017, 国防工业出版社 * |
| 机械工业部: "《中华人民共和国机械行业标准聚酰亚胺薄膜JB/T2726-1996》", 1 January 1997 * |
| 熊党生等: "《特种环境固体润滑涂层技术》", 31 July 2016, 国防工业出版社 * |
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