CN105038412A - Photosensitive graphene preparing method and ultraviolet light curing conductive ink - Google Patents
Photosensitive graphene preparing method and ultraviolet light curing conductive ink Download PDFInfo
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- 0 C*(C)C(CC(C)(C)C(C)(C)CC(C)(C)*(CCCC(*C(C(C)=*)=O)O)I)[n]1c2ccccc2c2c1cccc2 Chemical compound C*(C)C(CC(C)(C)C(C)(C)CC(C)(C)*(CCCC(*C(C(C)=*)=O)O)I)[n]1c2ccccc2c2c1cccc2 0.000 description 1
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Abstract
The invention discloses a photosensitive graphene preparing method and ultraviolet light curing conductive ink. According to the preparing method, double bonds are introduced to the graphene surface by adopting a photosensitive copolymer non-covalent modification method to obtain photosensitive graphene, the photosensitive graphene is added into an ultraviolet light curing prepolymer, the double bonds on the photosensitive graphene surface and double bonds in the ultraviolet light curing prepolymer interact for solidification crosslinking to obtain an ultraviolet light curing conductive coating with the graphene as filler. The obtained light curing ink has high electricity and heat conduction performance, and can meet the requirements for low electrical resistivity, large adhesive force and high hardness of an electronic line to be widely applied to different electronic information products such as a touch screen, an RFID and a flexible circuit.
Description
Technical field
The present invention relates to ultraviolet light polymerization and field of nanocomposite materials, be specifically related to a kind of preparation method and ultraviolet light polymerization electrically conductive ink of photosensitive Graphene.
Background technology
Electrically conductive ink belongs to functional special ink, existing electrically conductive ink is mainly filled-type, generally be made up of conductive filler material, resin matrix and dispersing additive and auxiliary agent etc., be printed on the ability non-conductive stock making it there is conduction current or get rid of accumulate static charge.What current commercial application was maximum is thermoplasticity or thermoset electrically conductive ink, generally needs pyroprocessing just can reach conduction requirement.This kind of ink, on the one hand containing solvent, exists and pollutes the problems such as large, toxicity is large, production process is dangerous, and inapplicable automatization large-scale pipeline is produced; On the other hand thermoplasticity or thermoset electrically conductive ink solidification value is high, precision and efficiency low, and be not suitable for the application on the heat-sensitive materials such as PET, PC, PVC.And German Bayer company is a kind of environmental protection, energy-efficient material cured technology in the UV-curing technology that the sixties in last century develop, be widely used in the exploitation of the functional materials such as anti-fouling material, self-repair material, microelectronic packaging material and sensing material in recent years, simultaneously because the feature of its low-temperature curing makes this curing technology particularly be applicable to the solidification of thermo-responsive base material functional material.What light curable conductive ink was the most frequently used is compound-type conducting material, and main conductive filler material and the photocureable polymer of adopting is composited.
Electrically conductive ink on market mainly comprises silver system electrically conductive ink, copper system electrically conductive ink and carbon series conductive ink.Silver system electrically conductive ink stable chemical nature, conducts electricity very well, but the formation conductive network that contacts with each other between conducting particles based on super fine silver powder, conductive filler material consumption, up to 65% ~ 75%, causes silver system electrically conductive ink to hold at high price.Copper system electrically conductive ink is cheap, but there is the shortcoming of oxidizable rear specific conductivity decline.Carbon series conductive ink is cheap, not oxidizable, environmental protection.Graphene is a kind of novel material of the individual layer sheet structure be made up of carbon atom, has extremely low resistivity and good snappiness, is applicable to very much for manufacturing flexible electron device etc.In addition, Graphene has high-specific surface area, easily forms conductive network, and the electrically conductive ink prepared using Graphene as conductive filler material has good electroconductibility and printing.But owing to there is strong Van der Waals force between graphene nanometer sheet and π-π interacts, cause it easily to reunite, bad dispersibility, the transmission for electric charge is very unfavorable.And graphenic surface is inertia, the dispersive ability in solvent and resin is limited, causes it in resin, be difficult to dispersion, poor with resin compatible, can not play its due characteristic.For matrix material, realize the key precondition that the dispersed and interfacial adhesion that strengthen between the two of filler in matrix resin is the excellent matrix material of processability.For solving the problem, surface modification being carried out to Graphene, while the proper property such as electricity, heat, mechanics keeping its excellence, improving its dispersing property in resin matrix and interface binding force is very urgent.
Summary of the invention
For the problems referred to above, applicant carries out non-covalent modification to Graphene, a kind of preparation method of photosensitive Graphene is provided, photosensitively improves its dispersiveness at light-cured resin giving it simultaneously, prepare ultraviolet light polymerization electrically conductive ink using photosensitive Graphene as filler.
The method is come grapheme modified by synthesizing a kind of novel photosensitive copolymers, simultaneously containing card azoles group and double bond in this polymkeric substance, pi-pi accumulation effect strong between card azoles group and Graphene impels polymkeric substance to be attracted to graphenic surface, thus introduces double bond to graphenic surface.The introducing of double bond group can not only strengthen the consistency of Graphene and epoxy resin, also imparts Graphene photosensitivity, jointly curing cross-linked can occur with the double bond in uv curable oligomer.Come grapheme modified by photosensitive copolymers like this, avoid the reunion of Graphene on the one hand, improve on the other hand and impart Graphene photocuring activity, enable to carry out photo-crosslinking with uv curable oligomer, such polymkeric substance is just as a bridge block, and stable for graphene uniform is dispersed in resin matrix by the reactive force relying on two ends to be formed, and forms conductive path, and link together securely with resin matrix, make it to become an organic whole.What obtained is filler with photosensitive Graphene UV curable ink has good electrical and thermal conductivity performance, can meet the requirement that electronic circuit resistivity is low, sticking power is large, hardness is high.
In order to achieve the above object, the preparation signal of photosensitive polymer of the present invention and structure are as shown in the formula (for vinylformic acid):
Wherein n=10 ~ 300, m=10 ~ 300, polymkeric substance number-average molecular weight between 3000 ~ 30,000, molecular weight distributing index is: 1.10 ~ 1.50.
Preparation method is as follows for this photosensitive polymer: by glycidyl methacrylate, vinylcarbazole, Diisopropyl azodicarboxylate, solvent, stirring and dissolving, logical N
25min ~ 30min, sealing, 50 ~ 100 DEG C of reaction 8 ~ 16h, be cooled to room temperature, a certain amount of methacrylic acid or vinylformic acid are joined in above-mentioned solution, then add catalyzer and promotor makes epoxide group open loop, 50 ~ 120 DEG C of reaction 8 ~ 16h, reaction terminates postprecipitation, and in vacuum drying oven, 20 ~ 80 DEG C of oven dry obtain the photosensitive copolymers that side chain contains double bond;
Graphene oxide is dispersed in DMF, adds hydrazine hydrate, 70 ~ 100 DEG C of reaction 8 ~ 12h, add photosensitive copolymers common distribution in a solvent, cool centrifugal, black powder is obtained after drying, for photosensitive copolymers is grapheme modified, i.e. photosensitive Graphene;
Finally mixed by the photosensitive Graphenes that step (2) is obtained by weight by the photosensitive prepolymer of 50 ~ 80%, 3 ~ 6% light initiation systems, 6 ~ 15% reactive thinners with 3.5 ~ 15%, stirred at ambient temperature is even, obtained UV curable ink.
In the preparation process of photosensitive polymer, glycidyl methacrylate, vinylcarbazole and acrylic acid mol ratio are 3: 1: 1-1: 2: 3, the amount of triphenylphosphine and Resorcinol (or Resorcinol) is respectively 1 ~ 3% and 0.5 ~ 1.5% of amount of monomer, solvent is solvent is tetrahydrofuran (THF), DMF, sherwood oil, ether, propylene oxide, acetone, chlorobenzene, dichlorobenzene, methylene dichloride, trichloromethane etc.
In the preparation process of photosensitive Graphene, the mass ratio of graphene oxide and photosensitive copolymers is 1: 1 ~ 1: 5, solvent is tetrahydrofuran (THF), DMF, sherwood oil, ether, propylene oxide, acetone, chlorobenzene, dichlorobenzene, methylene dichloride, trichloromethane etc.
In the preparation process of UV curable ink, described photosensitive prepolymer is a kind of unsaturated acrylic resin, is selected from photosensitive pure acrylic acid prepolymer, Epoxy Phenolic Acrylates prepolymer or polyurethane acrylate prepolymer further; Described reactive thinner is a kind of acrylate of polyfunctionality, can be selected from tri (propylene glycol) diacrylate, Viscoat 295 or pentaerythritol triacrylate; Described light trigger is one or more in 1-hydroxy cyclohexyl phenylketone, 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholine-1-acetone.
Advantageous Effects of the present invention is:
The present invention adopts photosensitive copolymers to carry out non covalent bond modification to Graphene and gives its photosensitivity, enable to carry out photo-crosslinking with uv curable oligomer, stable for graphene uniform is dispersed in resin matrix, forms conductive path, obtained light curable conductive ink.Have the following advantages:
1, adopt the method for multipolymer non covalent bond modification can give its photosensitivity while the electrical and thermal conductivity of maintenance Graphene own, method is simple, is easy to preparation in enormous quantities.
2, the modification of multipolymer effectively can also avoid the gathering of Graphene, improves its dispersing property in uv curable oligomer.
3, photosensitive Graphene can carry out photo-crosslinking with uv curable oligomer, make graphene uniform stable be dispersed in resin matrix, form conductive path, and to link together securely with resin matrix, make it to become an organic whole.The UV curable ink obtained has good electrical and thermal conductivity performance, can meet the requirement that electronic circuit resistivity is low, sticking power is large, hardness is high.
Embodiment
Set forth the present invention more specifically below in conjunction with embodiment and application examples, but the present invention is not limited thereto.
Embodiment 1:
(1) synthesis of photosensitive copolymers:
Glycidyl methacrylate 4.26g, vinylcarbazole 1.93g, Diisopropyl azodicarboxylate 0.071g are put into tetrahydrofuran (THF) stirring and dissolving together, logical N
2deoxygenation, sealing, 65 DEG C of reaction 15h, be cooled to room temperature, methacrylic acid 0.86g is joined in above-mentioned solution, then add catalyzer triphenylphosphine 0.062g and hydroquinone of polymerization retarder 0.035g, 90 DEG C of reaction 15h, reaction terminates postprecipitation, dries the photosensitive copolymers obtaining side chain and contain double bond in vacuum drying oven;
(2) preparation of photosensitive Graphene:
Graphene oxide 0.2g is dispersed in N, in dinethylformamide 40mL, add hydrazine hydrate 20 μ L, 70 DEG C of reaction 12h, add photosensitive copolymers 0.2g common distribution after cooling in a solvent, cooling centrifuge washing, obtains black powder after drying, for photosensitive copolymers is grapheme modified, i.e. photosensitive Graphene;
(3) based on the preparation of the UV curable ink of photosensitive Graphene:
Photosensitive polyurethane acrylic ester prepolymer 2.86g, 1-hydroxy cyclohexyl phenylketone 0.17g, tri (propylene glycol) diacrylate 0.38g are mixed with photosensitive Graphene 0.4g, stirred at ambient temperature is even, obtained UV curable ink.
Embodiment 2:
(1) synthesis of photosensitive copolymers:
Glycidyl methacrylate 1.42g, vinylcarbazole 1.93g, Diisopropyl azodicarboxylate 0.034g are put into ether stirring and dissolving together, logical N
2deoxygenation, sealing, 80 DEG C of reaction 12h, be cooled to room temperature, vinylformic acid 0.72g is joined in above-mentioned solution, then add catalyzer triphenylphosphine 0.081g and stopper Resorcinol 0.041g, 120 DEG C of reaction 8h, reaction terminates postprecipitation, dries the photosensitive copolymers obtaining side chain and contain double bond in vacuum drying oven;
(2) preparation of photosensitive Graphene:
Graphene oxide 0.1g is dispersed in N, in dinethylformamide 20mL, add hydrazine hydrate 10 μ L, 85 DEG C of reaction 10h, add photosensitive copolymers 0.2g common distribution after cooling in a solvent, cooling centrifuge washing, obtains black powder after drying, for photosensitive copolymers is grapheme modified, i.e. photosensitive Graphene;
(3) based on the preparation of the UV curable ink of photosensitive Graphene:
Mixed with photosensitive Graphene 0.2g by photosensitive prepolymer 3.2g, 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholine-1-acetone 0.12g, Viscoat 295 0.48g, stirred at ambient temperature is even, obtained UV curable ink.
Embodiment 3:
(1) synthesis of photosensitive copolymers:
Glycidyl methacrylate 1.42g, vinylcarbazole 3.86g, Diisopropyl azodicarboxylate 0.053g are put into trichloromethane stirring and dissolving together, logical N
2deoxygenation, sealing, 100 DEG C of reaction 8h, be cooled to room temperature, methacrylic acid 2.58g is joined in above-mentioned solution, then add catalyzer triphenylphosphine 0.236g and hydroquinone of polymerization retarder 0.118g, 85 DEG C of reaction 16h, reaction terminates postprecipitation, dries the photosensitive copolymers obtaining side chain and contain double bond in vacuum drying oven;
(2) preparation of photosensitive Graphene:
Graphene oxide 0.1g is dispersed in 40mLN, in dinethylformamide, add hydrazine hydrate 30 μ L, 100 DEG C of reaction 12h, add photosensitive copolymers 0.4g common distribution after cooling in a solvent, cooling centrifuge washing, obtains black powder after drying, for photosensitive copolymers is grapheme modified, i.e. photosensitive Graphene;
(3) based on the preparation of the UV curable ink of photosensitive Graphene:
Mixed with photosensitive Graphene 0.6g by photosensitive prepolymer 2.8g, 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholine-1-acetone 0.24g, pentaerythritol triacrylate 0.36g, stirred at ambient temperature is even, obtained UV curable ink.
Claims (4)
1. the preparation method of photosensitive Graphene and a ultraviolet light polymerization electrically conductive ink, is characterized in that preparation process is as follows:
(1) synthesis of photosensitive copolymers:
By glycidyl methacrylate, vinylcarbazole, Diisopropyl azodicarboxylate, solvent, stirring and dissolving, logical N25min ~ 30min, sealing, 50 ~ 100 DEG C of reaction 8 ~ 16h, be cooled to room temperature, a certain amount of methacrylic acid or vinylformic acid are joined in above-mentioned solution, then add catalyzer triphenylphosphine and hydroquinone of polymerization retarder or Resorcinol, 85 ~ 120 DEG C of reaction 8 ~ 16h, reaction terminates postprecipitation, and in vacuum drying oven, 20 ~ 80 DEG C of oven dry obtain the photosensitive copolymers that side chain contains double bond;
(2) preparation of photosensitive Graphene:
Graphene oxide is dispersed in DMF, adds hydrazine hydrate, 70 ~ 100 DEG C of reaction 8 ~ 12h, add photosensitive copolymers common distribution in a solvent after cooling, cooling centrifuge washing, black powder is obtained after drying, for photosensitive copolymers is grapheme modified, i.e. photosensitive Graphene;
(3) based on the preparation of the UV curable ink of photosensitive Graphene:
By weight the photosensitive prepolymer of 50 ~ 80%, 3 ~ 6% light initiation systems, 6 ~ 15% reactive thinners being mixed with 3.5 ~ 15% photosensitive Graphenes, stirred at ambient temperature is even, obtained UV curable ink.
2. the preparation method of photosensitive Graphene according to claim 1 and ultraviolet light polymerization electrically conducting coating, it is characterized in that: in the first step, the mol ratio of glycidyl methacrylate, vinylcarbazole and vinylformic acid (or methacrylic acid) is 3: 1: 1-1: 2: 3, the amount of triphenylphosphine and Resorcinol (or Resorcinol) is respectively 1 ~ 3% and 0.5 ~ 1.5% of amount of monomer, solvent is solvent is tetrahydrofuran (THF), DMF, sherwood oil, ether, propylene oxide, acetone, chlorobenzene, dichlorobenzene, methylene dichloride, trichloromethane etc.; Gained copolymer structure is represented by following general formula:
Wherein n=10 ~ 300, m=10 ~ 300, polymkeric substance number-average molecular weight between 3000 ~ 30,000, molecular weight distributing index is: 1.10 ~ 2.0.
3. the preparation method of photosensitive Graphene according to claim 1 and ultraviolet light polymerization electrically conductive ink, it is characterized in that: in second step, the mass ratio of graphene oxide and photosensitive copolymers is 1: 1 ~ 1: 5, solvent is tetrahydrofuran (THF), DMF, sherwood oil, ether, propylene oxide, acetone, chlorobenzene, dichlorobenzene, methylene dichloride, trichloromethane etc.
4. the preparation method of photosensitive Graphene according to claim 1 and ultraviolet light polymerization electrically conductive ink, it is characterized in that: described in the 3rd step, photosensitive prepolymer is a kind of unsaturated acrylic resin, be selected from photosensitive pure acrylic acid prepolymer, Epoxy Phenolic Acrylates prepolymer or polyurethane acrylate prepolymer further; Described reactive thinner is a kind of acrylate of polyfunctionality, can be selected from tri (propylene glycol) diacrylate, Viscoat 295 or pentaerythritol triacrylate; Described light trigger is one or more in 1-hydroxy cyclohexyl phenylketone, 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholine-1-acetone.
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| CN105575680A (en) * | 2016-01-29 | 2016-05-11 | 白德旭 | Graphene fiber supercapacitor and preparation method thereof |
| CN105647254A (en) * | 2016-01-15 | 2016-06-08 | 无锡市格林人造草坪有限公司 | Antibiosis oxidized graphene heat dissipation coating for artificial turf and preparing method thereof |
| CN106675075A (en) * | 2016-11-25 | 2017-05-17 | 安徽省春谷3D打印智能装备产业技术研究院有限公司 | Photosensitive resin material for 3D (Three-dimensional) printing and preparation method thereof |
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| CN105575680A (en) * | 2016-01-29 | 2016-05-11 | 白德旭 | Graphene fiber supercapacitor and preparation method thereof |
| CN106675075A (en) * | 2016-11-25 | 2017-05-17 | 安徽省春谷3D打印智能装备产业技术研究院有限公司 | Photosensitive resin material for 3D (Three-dimensional) printing and preparation method thereof |
| CN108301592A (en) * | 2017-01-11 | 2018-07-20 | 深圳市丰盛世纪实业有限公司 | A kind of more overheat pore passage structure heating floors |
| CN107384224A (en) * | 2017-08-24 | 2017-11-24 | 深圳市国创珈伟石墨烯科技有限公司 | A kind of graphene thermal conductivity UV glue and preparation method thereof |
| CN107805446A (en) * | 2017-11-10 | 2018-03-16 | 湖南辰砾新材料有限公司 | A kind of light curable conductive coating based on two-dimentional molybdenum disulfide and preparation method thereof |
| CN108003756A (en) * | 2017-12-13 | 2018-05-08 | 厦门中凯新材石墨烯科技有限公司 | A kind of storage tank liner graphene photocureable coating and its application method and preparation method |
| CN108795107A (en) * | 2018-03-24 | 2018-11-13 | 成都迪泰化工有限公司 | The method of modifying and its product and UV photocureable coating of a kind of graphene |
| CN109456437A (en) * | 2018-10-17 | 2019-03-12 | 东南大学 | A kind of spiral copolymer conductive material and preparation method thereof |
| CN109456437B (en) * | 2018-10-17 | 2021-01-05 | 东南大学 | Spiral copolymer conductive material and preparation method thereof |
| CN110083013A (en) * | 2019-04-19 | 2019-08-02 | 西安交通大学 | A kind of photocurable graphene oxide and preparation method thereof |
| WO2020211183A1 (en) * | 2019-04-19 | 2020-10-22 | 西安交通大学 | Photocurable graphene oxide and preparation method therefor |
| CN111234682A (en) * | 2020-01-17 | 2020-06-05 | 成都迪泰化工有限公司 | Photosensitive graphene oxide UV (ultraviolet) photocuring building coating and preparation method thereof |
| CN115947907A (en) * | 2022-12-30 | 2023-04-11 | 深圳市天祥新材料有限公司 | Graphene water reducing agent and preparation method and application thereof |
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