CN114276249A - Acrylic rosin resin, preparation method thereof and hydrofluoric acid-resistant UV resin prepared from acrylic rosin resin and used for electronic touch screen glass - Google Patents
Acrylic rosin resin, preparation method thereof and hydrofluoric acid-resistant UV resin prepared from acrylic rosin resin and used for electronic touch screen glass Download PDFInfo
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- CN114276249A CN114276249A CN202111672220.5A CN202111672220A CN114276249A CN 114276249 A CN114276249 A CN 114276249A CN 202111672220 A CN202111672220 A CN 202111672220A CN 114276249 A CN114276249 A CN 114276249A
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- hydrofluoric acid
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims abstract description 76
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 48
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 48
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229920005989 resin Polymers 0.000 title claims abstract description 45
- 239000011347 resin Substances 0.000 title claims abstract description 45
- 239000011521 glass Substances 0.000 title claims abstract description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000003085 diluting agent Substances 0.000 claims abstract description 12
- 239000007822 coupling agent Substances 0.000 claims abstract description 10
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 3
- MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- JRWNODXPDGNUPO-UHFFFAOYSA-N oxolane;prop-2-enoic acid Chemical group C1CCOC1.OC(=O)C=C JRWNODXPDGNUPO-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical group C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical group CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- -1 2,4, 6-trimethyl benzoyl ethyl Chemical group 0.000 claims description 3
- 230000001502 supplementing effect Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 abstract description 12
- 238000005530 etching Methods 0.000 abstract description 8
- 230000004224 protection Effects 0.000 abstract description 5
- 230000003993 interaction Effects 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 238000001723 curing Methods 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000011253 protective coating Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000006750 UV protection Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- CCOSOBKLKCHGNO-UHFFFAOYSA-N ethoxy-(2,4,6-trimethylbenzoyl)phosphinic acid Chemical compound C(C)OP(O)(=O)C(C1=C(C=C(C=C1C)C)C)=O CCOSOBKLKCHGNO-UHFFFAOYSA-N 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 150000004141 diterpene derivatives Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 208000034656 Contusions Diseases 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
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Abstract
The invention provides an acrylic rosin resin, a preparation method thereof and a hydrofluoric acid (UV) resistant resin prepared from the acrylic rosin resin for electronic touch screen glass, wherein the acrylic rosin resin has the following structure:
the hydrofluoric acid-resistant UV resin for the electronic touch screen glass comprises the following raw material components: 30-50 parts of acrylic rosin ester, 25-35 parts of diluent, 8-10 parts of coupling agent, 2-3 parts of accelerator and 3-5 parts of initiator. The UV protective ink adopts components with specific contents, can realize better interaction, and has better resistance to the prepared UV protective inkThe grinding characteristic can reduce the shallow scratch of the glass and is used for protecting an electronic glass screen; the method can be applied to the hydrofluoric acid etching protection of the electronic touch screen, and can resist 30% hydrofluoric acid for more than 15-25 minutes.
Description
Technical Field
The invention relates to an acrylic rosin resin, a preparation method thereof and a hydrofluoric acid (UV) resistant resin prepared from the acrylic rosin resin for electronic touch screen glass, and belongs to the technical field of protective printing ink.
Background
With the development of electronic technology, electronic touch screen glass is widely used. Electronic touch screen glass products can leave an indentation on glass in a series of processing and manufacturing processes such as cutting, CNC finishing impression, etching and the like, and sometimes can cause scratching, bruising, even breaking, and cause product quality problems and damage loss. Meanwhile, hydrofluoric acid thinning and etching are carried out on glass in the processing process of electronic touch screen glass products, and protection ink is generally adopted by technical personnel in the field to carry out processing protection and hydrofluoric acid etching thinning protection on glass touch screens.
The protective ink on the market at present mainly comprises thermosetting protective ink and UV protective ink. The thermosetting protective ink contains a solvent, so that a large amount of solvent is volatilized in the curing process, the production is not good for the health of workers, and the volatilization of the solvent can cause environmental pollution; the UV protection ink has received wide attention because of its fast curing speed and high production efficiency, especially because the solvent-free UV protection ink is environment-friendly. However, most of the existing UV system protective printing ink is not resistant to hydrofluoric acid etching, and is easy to cause damage of etched circuits, the main reason is that most of UV monomer resin in the existing market has poor adhesion to glass substrates and poor compactness, the prepared glass coating is soaked in 5% -30% hydrofluoric acid solution and usually falls off within 2 minutes, and hydrofluoric acid molecules are easy to permeate the protective coating to damage the circuits in the etching process.
Disclosure of Invention
The invention provides an acrylic rosin resin, a preparation method thereof and a hydrofluoric acid resistant UV resin for electronic touch screen glass prepared from the acrylic rosin resin.
More particularly, to hydrofluoric acid resistant UV protection ink for electronic touch screens, and preparation method and application thereof
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
an acrylic rosin resin has the following structure:
the acrylic rosin resin is used for preparing hydrofluoric acid resistant UV resin for electronic touch screen glass, and the inventor finds that a tricyclic diterpene structure in rosin can provide good adhesive force to a glass base material and the like, and the adhesion, hardness and wear resistance of a UV cured product can be improved by combining an epoxy resin benzene ring, and meanwhile, the adhesive force is promoted to be further improved; the double bonds are introduced to improve the crosslinking degree and molecular weight of the resin UV curing, so that the thermal stability and mechanical property of the film layer are improved; the synthesis process of the acrylic rosin resin is simple and convenient, the rosin and the epoxy can react under a mild condition, and the acrylic rosin resin can be obtained by controlling the proportion of reactants.
The preparation method of the acrylic rosin resin comprises the following steps:
1) reacting rosin with epoxy resin E51 at 80-100 ℃ by taking tetramethyl ammonium hydroxide pentahydrate as a catalyst until the acid value is less than 80mgKOH/g, wherein the rosin is hydrogenated rosin;
2) adding acrylic acid into the reaction material obtained in the step 1), supplementing tetramethyl ammonium hydroxide pentahydrate, and reacting at 80-100 ℃ until the acid value is less than 20 mgKOH/g.
In order to improve the product yield, in the step 1), the mass ratio of the rosin to the epoxy resin E51 is 1: (1-1.5); the mass consumption of the tetramethylammonium hydroxide pentahydrate is 2-8% of the mass of the rosin; the reaction time is 4-5 hours.
In order to improve the product yield and ensure the performance of the obtained UV resin, in the step 2), the mass ratio of acrylic acid to rosin in the step 1) is (0.15-0.3): 1, the mass amount of the supplemented tetramethylammonium hydroxide pentahydrate is 10-15% of the mass of the acrylic acid, and the reaction time is 3-4 hours.
The hydrofluoric acid resistant UV resin for the electronic touch screen glass comprises the following raw material components: 30-50 parts of acrylic rosin ester, 25-35 parts of diluent, 8-10 parts of coupling agent, 2-3 parts of accelerator and 3-5 parts of initiator, wherein the parts are in parts by mass.
The application of the hydrofluoric acid-resistant UV resin for the electronic touch screen glass comprises the following steps: screen-printing hydrofluoric acid resistant UV resin for electronic touch screen glass on glass, and curing under a mercury lamp or an LED lamp to obtain protective ink; the electronic touch screen glass is soaked in 5% -30% hydrofluoric acid solution after being cured by the hydrofluoric acid UV resistant resin, the protective film (the film layer formed after the hydrofluoric acid UV resin is cured) can not fall off after being continuously soaked for 15-25 minutes, the processing requirement is completely met, and the situation that hydrofluoric acid molecules penetrate through the protective coating to damage a circuit in the etching process is avoided.
The existing diluents, coupling agents, accelerators and initiators are various, however, not all commercial products have the same effect, and in order to further improve the hydrofluoric acid resistance, the diluents are tetrahydrofuran acrylate, the coupling agents are gamma-methacryloxypropyl trimethoxysilane, the accelerators are acryloyl morpholine, and the initiators are ethyl 2,4, 6-trimethylbenzoylphosphonate. By mixing and reacting the specific components with the acrylic rosin ester with a specific structure, the hydrofluoric acid resistance can be better ensured, and the alkali-soluble stripping property can be ensured. The selection of the diluent is more critical, the types of the diluents on the market are more, but in research and development practice, repeated experiments and comparisons show that the tetrahydrofuran acrylate has better solubility to the acrylic rosin ester with a specific structure, and after the tetrahydrofuran acrylate is compounded with other materials with specific components, the performance of the obtained UV resin is optimal.
According to the preparation method of the hydrofluoric acid resistant UV resin for the electronic touch screen glass, the acrylic rosin resin and the diluent are stirred for 5-10 hours at the temperature of 50-70 ℃, the temperature is reduced to room temperature, and the coupling agent, the accelerator and the initiator are added.
The prior art is referred to in the art for techniques not mentioned in the present invention.
The invention has the following beneficial effects:
1) the rosin acrylate is used as a main component, and the tricyclic diterpene rigid structure of rosin is combined with an epoxy resin benzene ring and the like, so that the product has good compactness, adhesive force and hydrofluoric acid resistance, the thermal stability and the mechanical property are remarkably improved, and the product cannot fall off after being soaked in 5-30% hydrofluoric acid solution for 15-25 minutes.
2) The preparation method of the UV protective ink provided by the invention is simple in process, free of solvent, environment-friendly, low in curing energy consumption, high in speed and suitable for large-scale application.
3) The UV protective ink can replace a solvent type hydrofluoric acid resistant protective coating after being cured.
Drawings
FIG. 1 is an infrared spectrum of a rosin ester acrylate of example 1 of the present invention;
Detailed Description
In order to better understand the present invention, the following examples are further provided to illustrate the present invention, but the present invention is not limited to the following examples.
Example 1
Accurately weighing hydrogenated rosin (30.446g,0.1mol), E51 epoxy resin (37.5g,0.1mol) and tetramethylammonium hydroxide pentahydrate (1.8123g,0.01mol), putting into a three-neck flask connected with mechanical stirring, connecting a reflux device, introducing nitrogen, raising the temperature to 90 ℃, reacting for 5 hours, reducing the acid value to be below 80mgKOH/g, adding acrylic acid (7.2g,0.1mol), supplementing the tetramethylammonium hydroxide pentahydrate (0.9062g,0.005mol), closing the nitrogen, reacting for 4 hours, reducing the acid value to be below 20mgKOH/g, and cooling to obtain the acrylic rosin ester. The infrared spectrum of the obtained rosin acrylate is shown in FIG. 1. 1928cm-1An ester bond absorption peak at 3512cm-1The hydroxyl absorption peak is 2932cm-1The absorption peak of the methyl methylene is that the acrylic acid rosin ester has the following structural characteristics:
example 2
Adding 50 g of acrylic rosin resin into a flask, adding 35 g of tetrahydrofuran acrylate serving as a diluent, heating to 50 ℃, stirring for 5 hours for dissolving, cooling the dissolved materials to room temperature, adding 8 g of gamma-methacryloxypropyltrimethoxysilane serving as a coupling agent, 3g of acryloylmorpholine serving as a promoter and 4 g of ethyl 2,4, 6-trimethylbenzoylphosphonate serving as an initiator, and uniformly stirring for later use.
Example 3
Adding 40 g of acrylic rosin resin into a flask, adding 30 g of tetrahydrofuran acrylate serving as a diluent, heating to 60 ℃, stirring for 5 hours for dissolving, cooling the dissolved materials to room temperature, adding 10 g of gamma-methacryloxypropyltrimethoxysilane serving as a coupling agent, 2g of acryloylmorpholine serving as a promoter and 3g of ethyl 2,4, 6-trimethylbenzoylphosphonate serving as an initiator, and uniformly stirring for later use.
Example 4
The UV resins prepared in examples 2 to 3 were each screen-printed (homogenized) onto glass plates at a coating thickness of 10 μm and cured with a UV lamp at a curing energy of about 2000mj/m2And all obtained compact glass coatings have the following properties: the coating has good glossiness, high hardness, good wear resistance and good heat resistance, and can better meet the processing protection requirements of electronic touch screen glass through practice verification, the product yield is obviously improved, and the coating can be quickly removed in a sodium hydroxide aqueous solution; the glass coating is placed in a 30% hydrofluoric acid solution, the temperature of the solution is 30 ℃, the falling time of the coating is observed, the glass coating does not turn white, wrinkle or fall off after being continuously soaked for 15-25 minutes, and the hydrofluoric acid does not permeate the coating, so that the hydrofluoric acid resistance of the glass coating is excellent, and the situation that hydrofluoric acid molecules permeate the protective coating to damage a circuit in the etching process can be effectively avoided.
Claims (8)
1. An acrylic rosin resin, characterized in that: the structure is as follows:
2. the method for producing an acrylic rosin resin according to claim 1, characterized in that: the method comprises the following steps:
1) reacting rosin with epoxy resin E51 at 80-100 ℃ by taking tetramethyl ammonium hydroxide pentahydrate as a catalyst until the acid value is less than 80mgKOH/g, wherein the rosin is hydrogenated rosin;
2) adding acrylic acid into the reaction material obtained in the step 1), supplementing tetramethyl ammonium hydroxide pentahydrate, and reacting at 80-100 ℃ until the acid value is less than 20 mgKOH/g.
3. The method of claim 2, wherein: in the step 1), the mass ratio of the rosin to the epoxy resin E51 is 1: (1-1.5); the mass consumption of the tetramethylammonium hydroxide pentahydrate is 2-8% of the mass of the rosin; the reaction time is 4-5 hours.
4. The production method according to claim 3 or 4, characterized in that: in the step 2), the mass ratio of acrylic acid to rosin in the step 1) is (0.15-0.3) to 1, the mass amount of the supplemented tetramethylammonium hydroxide pentahydrate is 10-15% of the mass of acrylic acid, and the reaction time is 3-4 hours.
5. The utility model provides an electron is hydrofluoric acid UV resistant resin for touch screen glass which characterized in that: the raw material components comprise: 30-50 parts of acrylic rosin ester, 25-35 parts of diluent, 8-10 parts of coupling agent, 2-3 parts of accelerator and 3-5 parts of initiator according to claim 1, wherein the parts are in parts by mass.
6. The use of the hydrofluoric acid-resistant UV resin for electronic touch screen glass according to claim 5, wherein: the electronic touch screen glass is printed on the glass through a hydrofluoric acid resistant UV resin screen, is cured under a mercury lamp or an LED lamp, and is soaked in a 5% -30% hydrofluoric acid solution after being cured, and the electronic touch screen glass cannot fall off after being soaked for 15-25 minutes.
7. The hydrofluoric acid resistant UV resin for electronic touch screen glass according to claim 5, wherein: the diluent is tetrahydrofuran acrylate, the coupling agent is gamma-methacryloxypropyl trimethoxy silane, the accelerator is acryloyl morpholine, and the initiator is 2,4, 6-trimethyl benzoyl ethyl phosphonate.
8. The method for preparing the hydrofluoric acid resistant UV resin for the electronic touch screen glass of claim 6 or 7, wherein the method comprises the following steps: stirring acrylic rosin resin and a diluent at 50-70 ℃ for 5-10 hours, cooling to room temperature, and adding a coupling agent, an accelerator and an initiator.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111672220.5A CN114276249B (en) | 2021-12-31 | 2021-12-31 | Acrylic rosin resin, preparation method thereof and hydrofluoric acid-resistant UV resin prepared from acrylic rosin resin for electronic touch screen glass |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111672220.5A CN114276249B (en) | 2021-12-31 | 2021-12-31 | Acrylic rosin resin, preparation method thereof and hydrofluoric acid-resistant UV resin prepared from acrylic rosin resin for electronic touch screen glass |
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| CN114276249A true CN114276249A (en) | 2022-04-05 |
| CN114276249B CN114276249B (en) | 2024-06-25 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040214987A1 (en) * | 2003-04-25 | 2004-10-28 | Kai-Uwe Gaudl | Acrylated natural resins |
| US20150337146A1 (en) * | 2014-05-21 | 2015-11-26 | Jetcoat Corporation | Aluminum chelate, method for manufacturing the same, and photocured ink including the same |
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2021
- 2021-12-31 CN CN202111672220.5A patent/CN114276249B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040214987A1 (en) * | 2003-04-25 | 2004-10-28 | Kai-Uwe Gaudl | Acrylated natural resins |
| US20150337146A1 (en) * | 2014-05-21 | 2015-11-26 | Jetcoat Corporation | Aluminum chelate, method for manufacturing the same, and photocured ink including the same |
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