CN105504960A - Beta-cyclodextrin and ruthenium complex and application of complex in microcontact printing technology - Google Patents
Beta-cyclodextrin and ruthenium complex and application of complex in microcontact printing technology Download PDFInfo
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- CN105504960A CN105504960A CN201511002431.2A CN201511002431A CN105504960A CN 105504960 A CN105504960 A CN 105504960A CN 201511002431 A CN201511002431 A CN 201511002431A CN 105504960 A CN105504960 A CN 105504960A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/025—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet
- B41M5/04—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet using solvent-soluble dyestuffs on the master sheets, e.g. alcohol-soluble
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/14—Printing inks based on carbohydrates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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Abstract
The invention relates to a ruthenium complex and further provides application of a beta-cyclodextrin and ruthenium complex composite solution in the microcontact printing technology. Beta-cyclodextrin is dissolved in water to obtain a beta-cyclodextrin water solution with the concentration of 3-6 g/L, 0.8g of ruthenium complex is added to each liter of beta-cyclodextrin water solution, then the frequency is adjusted to 20 kHz ultrasound for 30-60 min by an ultrasonic apparatus, and a PDMS seal is soaked with an obtained homodisperse beta-cyclodextrin and ruthenium complex composite solution and a carboxylation substrate is covered with the seal for electroless plating. According to the beta-cyclodextrin and ruthenium complex and the application of the complex in the microcontact printing technology, a new thought is provided for microcontact printing ink in preparing metal patterns in the surface of a polymer substrate frequently used in the electron industry and the microcontact printing industry.
Description
Technical field
The invention belongs to modern electronic technology field, particularly a kind of beta-cyclodextrin and ruthenium complexe are as the application of composite green Environment-friendlyink ink in microcontact printing techniques.
Background technology
Surface micro-constructing technology embody just gradually in significant application value, particularly microcontact printing techniques, its can in small size micro-patterning, in multiple field, particularly modern electronic technology field is significant.Current alternative micro-contact printing ink is less, and also limited to the material that micro-contact printing can be carried out in surface, a large amount of materials cannot prepare picture on surface by the method for micro-contact printing.Thus develop new, stable ink to have a very big significance.
The applicant discloses eight (pungent alkoxyl group)-Phthalocyanine Zinc carries out micro-contact printing in polyethylene terephthalate, Polyethylene Naphthalate or polyimide substrate utilisation technology as ink in authorized patent (CN102516841B); Water miscible 5 are disclosed in authorized patent (CN102964909B), 10,15,20-tetra-[4-(3 '-propoxy-pyridine Bromide) phenyl] zinc porphyrin carries out the utilisation technology in micro-contact printing in polyethylene terephthalate substrate; Water miscible 5,10,15,20-tetrasulfonic acid sodium phenyl zinc porphyrins carry out micro-contact printing utilisation technology in polyimide substrate is disclosed in authorized patent (CN102964910B).
For enriching the selection of micro-contact printing ink and substrate further, and promoting micro-contact printing quality, being necessary to develop beta-cyclodextrin and the application of ruthenium complexe in microcontact printing techniques further.Beta-cyclodextrin and the stable performance of ruthenium complexe composite solution, quality of forming film is high, can be applied to the micro-contact printing of surfaces of various materials as a kind of stable ink.
In order to adapt to the requirement of ink of new generation for environmental protection and HUMAN HEALTH, be necessary to develop the application of cyclodextrin in micro-contact printing further.Cyclodextrin is nontoxic, has good human compatibility.Beta-cyclodextrin and the stable performance of ruthenium complexe composite solution, quality of forming film is high, can be applied to the micro-contact printing of surfaces of various materials as a kind of stable ink.Current beta-cyclodextrin and ruthenium complexe composite solution have no report as the application of micro-contact printing ink.
Summary of the invention
The invention provides a kind of beta-cyclodextrin and ruthenium complexe as the application of composite green Environment-friendlyink ink in microcontact printing techniques.
Technical scheme of the present invention is as follows:
A kind of ruthenium complexe, it is characterized in that, the structural formula of described title complex is:
The chemical name of this compound: chlorine one (1E, 3Z, 6E)-1,7-bis-(3,4-Dimethoxyphenyl)-4-(vinyl)-1,3,6-heptantriene-3, a 5-diketone monomethyl isopropyl benzene closes ruthenium.
The application in microcontact printing techniques of beta-cyclodextrin and ruthenium complexe, is characterized in that, comprise the steps:
1) substrate surface process: the isopropanol water solution immersion 30-60min by polymeric substrates mass percent being 45-55%, 2-3mol/L sulphuric acid soln is placed in again after taking-up, and 15-20min is soaked under temperature is 55-65 DEG C of condition, clean with water subsequently, be carry out vacuum-drying under the condition of 60-65 DEG C in temperature, introduce carboxyl at polymer-based carbon basal surface, obtain carboxylated substrate;
2) beta-cyclodextrin and ruthenium complexe composite solution is prepared: by beta-cyclodextrin water dissolution, obtain the beta-cyclodextrin aqueous solution that concentration is 3-6g/L, 0.8g ruthenium complexe is added in often liter of beta-cyclodextrin aqueous solution, then by ultrasonic apparatus by frequency for arranging the ultrasonic 30-60min of 20kHz, obtain homodisperse beta-cyclodextrin and ruthenium complexe composite solution;
3) micro-contact printing: PDMS seal is soaked in 30-40s in beta-cyclodextrin and ruthenium complexe composite solution, in N after taking-up
2dry 30-60s in air-flow, is placed on the PDMS seal scribbling beta-cyclodextrin and ruthenium complexe composite solution in carboxylated substrate, gently presses 10-20s, PDMS seal designs is transferred to carboxylated substrate surface, obtains printing figuratum substrate;
4) electroless plating: figuratum for print substrate is soaked in 0.1-0.3g/LPdCl
210-30s in solution, is put in after taking-up in chemical plating solution and carries out electroless plating, and the time is 1-10min, obtains exquisite metallic copper pattern after taking-up in substrate.
Preferably, the application in microcontact printing techniques of described beta-cyclodextrin and ruthenium complexe, is characterized in that, step 1) in the polymeric base material selected be polyethylene terephthalate.
Preferably, the application in microcontact printing techniques of described beta-cyclodextrin and ruthenium complexe, is characterized in that, step 1) in the mass percent of the aqueous isopropanol selected and polymeric substrates be 1: 1-5.
Preferably, the application in microcontact printing techniques of described beta-cyclodextrin and ruthenium complexe, it is characterized in that, step 4) in chemical plating solution can be the chemical plating solution be made up of the distilled water of 4-6wt% copper sulfate, 7-8wt% sodium-potassium tartrate, 6-10wt% sodium hydroxide, 32-36wt% formaldehyde and surplus.
Preferably, the application in microcontact printing techniques of described beta-cyclodextrin and ruthenium complexe, it is characterized in that, step 4) in chemical plating solution can be the chemical plating solution be made up of the distilled water of 5-8wt% gold perchloride, 5-8wt% gold sodium sulfide, 10-12wt% S-WAT, 15-18wt% Tripotassium Citrate and surplus.
Beneficial effect of the present invention:
1) beta-cyclodextrin has good biocompatibility, and the material obtained after micro-contact printing has the potentiality used in human body as bio-medical material.
2) beta-cyclodextrin intramolecule is a hydrophobic cavities in " V " font, is applicable to holding ruthenium complexe molecule and enters and be fixed on beta-cyclodextrin intramolecule; Utilize the coordination of gold and carboxyl to combine and form stable mixture, thus act in polymeric substrates, be connected with the carboxyl coordination in polymeric substrates, form there Thermodynamically stable, Ordered Film that energy is low on the surface of the substrate, the strong metal ion adsorbed in chemical plating solution, define exquisite pattern, use when beta-cyclodextrin and the printing of ruthenium complexe composite solution simultaneously and there will not be molecular diffusion, cause the phenomenons such as pattern distortions broadens to occur.
3) by beta-cyclodextrin and ruthenium complexe composite solution are prepared metal pattern, for micro-contact printing industry provides new approaches as micro-contact printing ink at the polymer-based carbon basal surface that electron trade is conventional.
4) beta-cyclodextrin and ruthenium complexe composite solution, environmental protection, harmless nontoxic, cell survival rate is high.
5) beta-cyclodextrin and ruthenium complexe composite solution raw material is easy to get, cost is low, stable, industrial application has very large potentiality.
Embodiment
Following examples further illustrate of the present invention, but absolutely not limit the scope of the present invention.Elaborate the present invention further referring to embodiment, but it will be appreciated by those skilled in the art that the present invention is not limited to the preparation method of these embodiments and use.And those skilled in the art can carry out equivalent replacement, combination, improvement to the present invention according to description of the invention or modify, and these all comprise within the scope of the invention.
Embodiment 1
1) substrate surface process: be the isopropanol water solution immersion 30min of 45% by polyethylene terephthalate mass percent, wherein, the mass percent of aqueous isopropanol and polyethylene terephthalate is 1: 1,2mol/L sulphuric acid soln is placed in again after taking-up, and 15min is soaked under temperature is 55 DEG C of conditions, clean with water subsequently, be carry out vacuum-drying under the condition of 60 DEG C in temperature, introduce carboxyl at polymer-based carbon basal surface, obtain carboxylated PET substrate;
2) beta-cyclodextrin and ruthenium complexe composite solution is prepared: by beta-cyclodextrin water dissolution, obtain the beta-cyclodextrin aqueous solution that concentration is 3g/L, 0.8g ruthenium complexe is added in often liter of beta-cyclodextrin aqueous solution, then by ultrasonic apparatus by frequency for arranging the ultrasonic 30min of 20kHz, obtain homodisperse beta-cyclodextrin and ruthenium complexe composite solution;
3) micro-contact printing: PDMS seal is soaked in 30s in beta-cyclodextrin and ruthenium complexe composite solution, after taking-up in N2 air-flow dry 30s, the PDMS seal scribbling beta-cyclodextrin and ruthenium complexe composite solution is placed in carboxylated substrate, light pressure 10s, PDMS seal designs is transferred to carboxylated substrate surface, obtains printing figuratum substrate;
4) electroless plating: figuratum for print substrate is soaked in 0.1g/LPdCl
210s in solution, be put in after taking-up in the chemical bronze plating liquid be made up of the distilled water of 4wt% copper sulfate, 7wt% sodium-potassium tartrate, 6wt% sodium hydroxide, 32wt% formaldehyde and surplus and carry out electroless plating, time is 1min, can obtain exquisite metallic copper pattern after taking-up in substrate.
The pattern fineness drawn is careful, neatly complete, distortionless, and diffusion deformation phenomenon occurs.
Embodiment 2
1) substrate surface process: be the isopropanol water solution immersion 60min of 55% by polyethylene terephthalate mass percent, wherein, the mass percent of aqueous isopropanol and polyethylene terephthalate is 1: 5,3mol/L sulphuric acid soln is placed in again after taking-up, and 20min is soaked under temperature is 65 DEG C of conditions, clean with water subsequently, be carry out vacuum-drying under the condition of 65 DEG C in temperature, introduce carboxyl at polymer-based carbon basal surface, obtain carboxylated PET substrate;
2) beta-cyclodextrin and ruthenium complexe composite solution is prepared: by beta-cyclodextrin water dissolution, obtain the beta-cyclodextrin aqueous solution that concentration is 6g/L, 0.8g ruthenium complexe is added in often liter of beta-cyclodextrin aqueous solution, then by ultrasonic apparatus by frequency for arranging the ultrasonic 60min of 20kHz, obtain homodisperse beta-cyclodextrin and ruthenium complexe composite solution;
3) micro-contact printing: PDMS seal is soaked in 40s in beta-cyclodextrin and ruthenium complexe composite solution, after taking-up in N2 air-flow dry 60s, the PDMS seal scribbling beta-cyclodextrin and ruthenium complexe composite solution is placed in carboxylated substrate, light pressure 20s, PDMS seal designs is transferred to carboxylated substrate surface, obtains printing figuratum substrate;
4) electroless plating: figuratum for print substrate is soaked in 0.3g/LPdCl
230s in solution, be put in after taking-up in the chemical gold plating liquid be made up of the distilled water of 5% gold perchloride, 5% gold sodium sulfide, 10% S-WAT, 15% Tripotassium Citrate and surplus and carry out electroless plating, time is 10min, can obtain exquisite metallic gold pattern after taking-up in substrate.
The pattern fineness drawn is careful, neatly complete, distortionless, and diffusion deformation phenomenon occurs.
Embodiment 3
Human normal epidermic cell HaCaT is incubated in DMEM (DMEM) nutrient solution (containing 10% new-born calf serum), puts 37 DEG C, 5%CO
2cultivate under condition, 1 ~ 2d changes 1 nutrient solution.When Growth of Cells to logarithmic phase add respectively embodiment 1, embodiment 2 obtain metal pattern substrate and carboxylated before PET substrate process.Cell 0.25% Trypsin 96 orifice plate is placed in 37 DEG C, 5%CO
2incubator is cultivated.After 2 ~ 4h, every block culture plate add respectively embodiment 1, embodiment 2 obtain metal pattern substrate and carboxylated before PET substrate and complete culture solution cultured cells as experimental group and control group, containing cell and nutrient solution as blank, culture plate is moved into 37 DEG C, 5%CO
2incubator is cultivated.After 24h, abandon nutrient solution, phosphate buffered saline buffer (PBS) washes plate 2 times, adds 2-(2-methoxyl group-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfonic acid benzene)-2H-tetrazolium monosodium salt (CCK-8) 10 μ l.Continue at 37 DEG C, 5%CO
2incubator is cultivated 2 ~ 4h, microplate reader 550nm place and is surveyed each hole optical density(OD) (D value).Cell survival rate (%)=[(experimental port D value-blank well D value)/(control wells D value-blank well D value)] × 100%.
Blank group: 100%
Control group: the PET substrate 80.2% before carboxylated
Experimental group: (comprising embodiment 1 and embodiment 2)
Embodiment 1:98.9%
Embodiment 2:99.2%
Beta-cyclodextrin and ruthenium complexe composite solution, environmental protection, harmless nontoxic, cell survival rate is high.
Although embodiment of the present invention are open as above, but it is not restricted to listed in specification sheets and embodiment utilization, it can be applied to various applicable the field of the invention completely, for those skilled in the art, can easily realize other amendment, therefore do not deviating under the universal that claim and equivalency range limit, the present invention is not limited to specific details and illustrates here and the embodiment described.
Claims (6)
1. a ruthenium complexe, is characterized in that, the structural formula of described title complex is:
The chemical name of this compound: chlorine one (1E, 3Z, 6E)-1,7-bis-(3,4-Dimethoxyphenyl)-4-(vinyl)-1,3,6-heptantriene-3, a 5-diketone monomethyl isopropyl benzene closes ruthenium.
2. beta-cyclodextrin and the ruthenium complexe application in microcontact printing techniques, is characterized in that, comprise the steps:
1) substrate surface process: the isopropanol water solution immersion 30-60min by polymeric substrates mass percent being 45-55%, 2-3mol/L sulphuric acid soln is placed in again after taking-up, and 15-20min is soaked under temperature is 55-65 DEG C of condition, clean with water subsequently, be carry out vacuum-drying under the condition of 60-65 DEG C in temperature, introduce carboxyl at polymer-based carbon basal surface, obtain carboxylated substrate;
2) beta-cyclodextrin and ruthenium complexe composite solution is prepared: by beta-cyclodextrin water dissolution, obtain the beta-cyclodextrin aqueous solution that concentration is 3-6g/L, 0.8g ruthenium complexe is added in often liter of beta-cyclodextrin aqueous solution, then by ultrasonic apparatus by frequency for arranging the ultrasonic 30-60min of 20kHz, obtain homodisperse beta-cyclodextrin and ruthenium complexe composite solution;
3) micro-contact printing: PDMS seal is soaked in 30-40s in beta-cyclodextrin and ruthenium complexe composite solution, in N after taking-up
2dry 30-60s in air-flow, is placed on the PDMS seal scribbling beta-cyclodextrin and ruthenium complexe composite solution in carboxylated substrate, gently presses 10-20s, PDMS seal designs is transferred to carboxylated substrate surface, obtains printing figuratum substrate;
4) electroless plating: figuratum for print substrate is soaked in 0.1-0.3g/LPdCl
210-30s in solution, is put in after taking-up in chemical plating solution and carries out electroless plating, and the time is 1-10min, obtains exquisite metallic copper pattern after taking-up in substrate.
3. beta-cyclodextrin as claimed in claim 2 and the application of ruthenium complexe in microcontact printing techniques, is characterized in that, step 1) in the polymeric base material selected be polyethylene terephthalate.
4. beta-cyclodextrin as claimed in claim 2 and the application of ruthenium complexe in microcontact printing techniques, is characterized in that, step 1) in the mass percent of the aqueous isopropanol selected and polymeric substrates be 1: 1-5.
5. beta-cyclodextrin and the ruthenium complexe application in microcontact printing techniques as claimed in claim 2, it is characterized in that, step 4) in chemical plating solution can be the chemical plating solution be made up of the distilled water of 4-6wt% copper sulfate, 7-8wt% sodium-potassium tartrate, 6-10wt% sodium hydroxide, 32-36wt% formaldehyde and surplus.
6. beta-cyclodextrin as claimed in claim 2 and the application of ruthenium complexe in microcontact printing techniques, it is characterized in that, step 4) in chemical plating solution can be the chemical plating solution be made up of the distilled water of 5-8wt% gold perchloride, 5-8wt% gold sodium sulfide, 10-12wt% S-WAT, 15-18wt% Tripotassium Citrate and surplus.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0952463A (en) * | 1995-08-10 | 1997-02-25 | Riso Kagaku Corp | Fixing method of printing water base ink and water base ink |
| CN104312262A (en) * | 2014-11-05 | 2015-01-28 | 广西师范学院 | Application of 2-6 carboxyl phthalocyanine palladium and anthraquinone serving as micro-contact printing ink |
| CN104370971A (en) * | 2014-10-28 | 2015-02-25 | 广西师范学院 | Cyanovinyl ruthenium compound as well as preparation method and application thereof |
| CN104447820A (en) * | 2014-11-05 | 2015-03-25 | 广西师范学院 | Water-soluble double-layer sandwich-type Ce metalloporphyrin complex and application of complex in microcontact printing technique |
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- 2015-12-28 CN CN201511002431.2A patent/CN105504960B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0952463A (en) * | 1995-08-10 | 1997-02-25 | Riso Kagaku Corp | Fixing method of printing water base ink and water base ink |
| CN104370971A (en) * | 2014-10-28 | 2015-02-25 | 广西师范学院 | Cyanovinyl ruthenium compound as well as preparation method and application thereof |
| CN104312262A (en) * | 2014-11-05 | 2015-01-28 | 广西师范学院 | Application of 2-6 carboxyl phthalocyanine palladium and anthraquinone serving as micro-contact printing ink |
| CN104447820A (en) * | 2014-11-05 | 2015-03-25 | 广西师范学院 | Water-soluble double-layer sandwich-type Ce metalloporphyrin complex and application of complex in microcontact printing technique |
Non-Patent Citations (2)
| Title |
|---|
| 张礼和: "《化学学科进展》", 31 August 2005, 化学工业出版社 * |
| 郑姗姗: "《新型联吡啶钌环糊精衍生物的荧光特性及对维生素类壳体小分子的主客体识别作用的研究》", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
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Effective date of registration: 20191016 Address after: 314500 Building 1, Chongfu Industrial Zone, Tongxiang City, Jiaxing City, Zhejiang Province Patentee after: ZHEJIANG DONGHE PRINTING PACKAGING Co.,Ltd. Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee before: Nanning Normal University |