CN116285498B - High-temperature-resistant UV (ultraviolet) inkjet printing ink - Google Patents
High-temperature-resistant UV (ultraviolet) inkjet printing ink Download PDFInfo
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- CN116285498B CN116285498B CN202310453063.1A CN202310453063A CN116285498B CN 116285498 B CN116285498 B CN 116285498B CN 202310453063 A CN202310453063 A CN 202310453063A CN 116285498 B CN116285498 B CN 116285498B
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- 238000007641 inkjet printing Methods 0.000 title claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- -1 modified acrylic ester Chemical class 0.000 claims abstract description 23
- 239000012265 solid product Substances 0.000 claims abstract description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 20
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 20
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 19
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 19
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 19
- 238000010521 absorption reaction Methods 0.000 claims description 15
- 238000012544 monitoring process Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 238000002390 rotary evaporation Methods 0.000 claims description 15
- 238000005259 measurement Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 230000001678 irradiating effect Effects 0.000 claims description 10
- 239000011259 mixed solution Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims description 5
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 claims description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N ethylene glycol diacrylate Substances C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 15
- 239000011248 coating agent Substances 0.000 abstract description 13
- 238000005336 cracking Methods 0.000 abstract description 5
- 238000007796 conventional method Methods 0.000 abstract description 2
- 239000000976 ink Substances 0.000 description 40
- 238000007639 printing Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 229910000679 solder Inorganic materials 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 238000007650 screen-printing Methods 0.000 description 4
- 238000001723 curing Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention belongs to the technical field of coatings, and particularly relates to high-temperature-resistant UV (ultraviolet) inkjet printing ink. In order to meet the requirement of low viscosity of ink-jet printing, the common ink-jet printing ink has the advantages that the addition amount of a low-molecular-weight small-molecular acrylate monomer in the formula is too high, the high-temperature resistance of a cured ink coating is poor, and high-temperature cracking is easy to occur. In order to solve the problems, the invention provides high-temperature-resistant UV (ultraviolet) inkjet printing ink, wherein modified acrylic ester added in the formula is hyperbranched organic-inorganic hybrid acrylic ester oligomer formed by a solid product A and acrylic ester monomers, the surface of the solid product A contains rich hyperbranched points (mercapto groups), the viscosity of the hyperbranched acrylic ester oligomer formed by the reaction with the acrylic ester monomers is lower than that of the hyperbranched organic-inorganic hybrid acrylic ester oligomer prepared by a conventional method, and the content of low-molecular-weight acrylic ester monomers in an ink system is reduced more favorably, so that the high-temperature cracking resistance of an ink cured coating is improved.
Description
Technical Field
The invention belongs to the technical field of ink-jet printing ink, and particularly relates to high-temperature-resistant UV ink-jet printing ink.
Background
In recent years, the digital ink-jet industry is rapidly developed, and UV ink-jet is a digital ink-jet technology utilizing ultraviolet curing, and has the advantages of simple operation, wide applicable medium, no need of post-treatment, energy conservation, environmental protection and the like. UV inkjet was developed on the basis of UV curable printing inks, the same principle of operation as UV curable printing inks.
A Printed Circuit Board (PCB) is a support for electronic components and is a carrier for electrical connection of the electronic components. In order to protect the non-soldered portion from damage during the production process of the PCB, protection with high temperature resistant solder resist ink is required. At present, PCB solder resist ink is usually ultraviolet light curing ink, screen printing is needed when the PCB solder resist ink is used, and a screen printing plate with pictures and texts is manufactured through a photosensitive plate making method, so that the process is relatively complex, a large amount of waste water can be generated in the production process, and raw materials are seriously wasted.
The ink-jet printing technology is a printing mode which adopts a non-contact, non-pressure and non-printing plate mode, and is relatively simple to operate. Compared with screen printing, the ink-jet printing omits the step of developing in the screen printing, thereby reducing the waste of a large amount of raw materials and the generation of industrial wastewater, meeting the current environmental protection requirement, and being a novel process with low pollution and high raw material utilization rate.
The ink-jet printing technology has higher requirements on the viscosity of ink, the viscosity of the ink is too high, nozzles are easy to block, normal continuous ink-jet printing cannot be realized, in order to meet the requirements on low viscosity of ink-jet printing, the addition amount of a low-molecular-weight small-molecular acrylate monomer in a formula of the common ink-jet printing ink is too high, the addition amount of a high-molecular-weight matrix resin is too small, the addition amount of the matrix resin is about 10%, and therefore, the high-temperature resistance of the common ink-jet printing ink coating is poor, and the ink coating is easy to crack under a high-temperature environment.
Disclosure of Invention
The problems in the prior art are: in order to meet the requirement of low viscosity of ink-jet printing, the common ink-jet printing ink has the advantages that the addition amount of a low molecular weight small molecular acrylate monomer in a formula is too high, the high-temperature resistance of a cured ink coating is poor, and high-temperature cracking is easy to occur, and the high-temperature resistant UV ink-jet printing ink provided by the invention comprises the following components in percentage by weight:
specifically, the preparation method of the modified acrylic ester comprises the following steps:
(1) Mixing KH590, absolute ethyl alcohol and water in a three-neck flask according to a volume ratio of 3:1:5, regulating the pH value of the solution to be 3-6 by using glacial acetic acid, then heating the reaction system to 60 ℃, stirring and reacting for 2 hours under the protection of nitrogen, and then carrying out vacuum rotary evaporation and drying on the reaction product to obtain a solid product A with rich mercapto on the surface;
(2) Mixing a solid product A and toluene in a flask according to a mass ratio of 1:4, dropwise adding a photoinitiator 1173 while stirring, wherein the dropwise adding amount of the photoinitiator 1173 is 2% of the mass of the solid product A, then heating a reaction system to 50 ℃, dropwise adding a toluene solution with the mass percent of 4- (3-methyl-2-buten-2-yl) benzoic acid content of 20% into the reaction system under the protection of nitrogen, dropwise adding and stirring, irradiating with an LED lamp with a wavelength of 365nm, monitoring the reaction by FTIR measurement, and obtaining a mixed liquid B when a mercapto absorption peak in the reaction system disappears;
(3) Adding 10.8g of 3-mercapto-1, 2-propanediol into a flask, adding 1173 g of photoinitiator and 70mL of toluene, stirring uniformly, then heating the flask to 50 ℃, dropwise adding 50% butyl acetate solution of THEICTA (total internal heat transfer coefficient) by mass percent under the protection of nitrogen, irradiating with an LED lamp with the wavelength of 365nm while monitoring the reaction by FTIR (FTIR), and removing the solvent by rotary evaporation to obtain a product C when the mercapto absorption peak in the reaction system disappears;
(4) And (3) heating the mixed solution B to 100 ℃, then adding a butyl acetate solution containing a product C and p-toluenesulfonic acid into the mixed solution B in a dropwise manner while stirring, monitoring the reaction through FTIR measurement, and carrying out vacuum rotary evaporation and drying on a reaction product after the carboxyl absorption peak in the reaction system disappears, thereby obtaining the modified acrylic resin, wherein the mass percentage of the product C in the butyl acetate is 30%, and the addition amount of the p-toluenesulfonic acid is 1% of the mass of the product C in the butyl acetate solution.
Specifically, the pigment is nano white color paste.
Specifically, the photoinitiator includes at least one of a photoinitiator 184, TPO, 1173, 819.
Specifically, the dispersing agent comprises at least one of the humus DP983, BYK168 and dygao 710.
Specifically, the acrylate monomer comprises at least one of pentaerythritol tetraacrylate, 1, 6-ethylene glycol diacrylate and tripropylene glycol diacrylate.
Specifically, the preparation method comprises the following steps:
under the condition of avoiding light, the components are mixed and stirred uniformly according to the formula amount, and the product is obtained.
The invention has the following beneficial effects:
(1) The modified acrylic ester prepared by the invention is hyperbranched organic-inorganic hybrid acrylic ester oligomer formed by a solid product A and an acrylic ester monomer, the surface of the solid product A contains rich hyperbranched points (mercapto groups), and the viscosity of the hyperbranched acrylic ester oligomer formed by the reaction with the acrylic ester monomer is lower than that of the hyperbranched organic-inorganic hybrid acrylic ester oligomer prepared by a conventional method, so that the content of the low molecular weight acrylic ester monomer in an ink system is reduced more favorably, and the high-temperature cracking resistance of the ink cured coating is improved;
(2) The hyperbranched organic-inorganic hybrid acrylate oligomer structure contains a large amount of benzene rings and nitrogen-containing six-membered heterocyes, the nitrogen-containing six-membered heterocyes have the property of aromatic rings, the benzene rings and the nitrogen-containing six-membered heterocyes both contain cyclic structures with large pi bonds, favorable pi-pi interactions are generated between the structures, and the high temperature resistance and the weather resistance of the coating can be obviously improved;
(3) The hyperbranched organic-inorganic hybrid acrylate oligomer structure contains an inorganic silica structure, can reduce the cohesive force of the ink cured coating under the high-temperature condition, and is very beneficial to further improving the high-temperature cracking resistance of the ink cured coating.
The specific embodiment is as follows:
the present invention will be described in detail with reference to examples. It is to be understood that the following examples are illustrative of embodiments of the present invention and are not intended to limit the scope of the invention.
The modified acrylates in the following examples of the invention were prepared as follows:
(1) Mixing KH590, absolute ethyl alcohol and water in a three-neck flask according to a volume ratio of 3:1:5, regulating the pH value of the solution to be=5 by using glacial acetic acid, then heating the reaction system to 60 ℃, stirring and reacting for 2 hours under the protection of nitrogen, and then carrying out vacuum rotary evaporation and drying on the reaction product to obtain a solid product A with rich mercapto on the surface;
(2) Mixing a solid product A and toluene in a flask according to a mass ratio of 1:4, dropwise adding a photoinitiator 1173 while stirring, wherein the dropwise adding amount of the photoinitiator 1173 is 2% of the mass of the solid product A, then heating a reaction system to 50 ℃, dropwise adding a toluene solution with the mass percent of 4- (3-methyl-2-buten-2-yl) benzoic acid content of 20% into the reaction system under the protection of nitrogen, dropwise adding and stirring, irradiating with an LED lamp with a wavelength of 365nm, monitoring the reaction by FTIR measurement, and obtaining a mixed liquid B when a mercapto absorption peak in the reaction system disappears;
(3) Adding 10.8g of 3-mercapto-1, 2-propanediol into a flask, adding 1173 g of photoinitiator and 70mL of toluene, stirring uniformly, then heating the flask to 50 ℃, dropwise adding 50% butyl acetate solution of THEICTA (total internal heat transfer coefficient) by mass percent under the protection of nitrogen, irradiating with an LED lamp with the wavelength of 365nm while monitoring the reaction by FTIR (FTIR), and removing the solvent by rotary evaporation to obtain a product C when the mercapto absorption peak in the reaction system disappears;
(4) And (3) heating the mixed solution B to 100 ℃, then adding a butyl acetate solution containing a product C and p-toluenesulfonic acid into the mixed solution B in a dropwise manner while stirring, monitoring the reaction through FTIR measurement, and carrying out vacuum rotary evaporation and drying on a reaction product after the carboxyl absorption peak in the reaction system disappears, thereby obtaining the modified acrylic resin, wherein the mass percentage of the product C in the butyl acetate is 30%, and the addition amount of the p-toluenesulfonic acid is 1% of the mass of the product C in the butyl acetate solution.
The pigment used in the following examples of the present invention is a nano white paste, with the brand name D401, purchased from Dongguan color name coating technology Co.
Example 1
The high-temperature-resistant UV ink-jet printing ink comprises the following components in percentage by weight:
example 2
The high-temperature-resistant UV ink-jet printing ink comprises the following components in percentage by weight:
example 3
The high-temperature-resistant UV ink-jet printing ink comprises the following components in percentage by weight:
example 4
The high-temperature-resistant UV ink-jet printing ink comprises the following components in percentage by weight:
example 5
The high-temperature-resistant UV ink-jet printing ink comprises the following components in percentage by weight:
example 6
The high-temperature-resistant UV ink-jet printing ink comprises the following components in percentage by weight:
comparative example 1 the same as example 1 was different in that comparative example 1 replaced the modified acrylate of example 1 with a hyperbranched modified acrylate prepared according to the following steps:
1mol of IPDI, 2mol of trimethylolpropane and 2mol of methacryloxyethyl isocyanate are added into a three-necked flask, then 2mol of dibutyltin dilaurate and 100mL of tetrahydrofuran are added, and stirring reaction is carried out for 6 hours at 50 ℃ to obtain hyperbranched polyurethane methacrylic resin, the yield is 92%, the number average molecular weight is 2900, and the grafting rate of methacryloxygroups is 66%.
Comparative example 2 the same as example 1, except that the modified acrylate of comparative example 2 was prepared according to the following procedure:
(1) Mixing KH590, absolute ethyl alcohol and water in a three-neck flask according to a volume ratio of 3:1:5, regulating the pH value of the solution to be=5 by using glacial acetic acid, then heating the reaction system to 60 ℃, stirring and reacting for 2 hours under the protection of nitrogen, and then carrying out vacuum rotary evaporation and drying on the reaction product to obtain a solid product A with rich mercapto on the surface;
(2) Mixing a solid product A and toluene in a flask according to a mass ratio of 1:4, dropwise adding a photoinitiator 1173 while stirring, wherein the dropwise adding amount of the photoinitiator 1173 is 2% of the mass of the solid product A, then, heating a reaction system to 50 ℃, dropwise adding a toluene solution with 20% of acrylic acid mass percent into the reaction system under the protection of nitrogen, dropwise adding while stirring, irradiating with an LED lamp with a wavelength of 365nm, monitoring the reaction by FTIR measurement, and obtaining a mixed liquid B when a mercapto absorption peak in the reaction system disappears;
(3) Adding 10.8g of 3-mercapto-1, 2-propanediol into a flask, adding 1173 g of photoinitiator and 70mL of toluene, stirring uniformly, then heating the flask to 50 ℃, dropwise adding 50% butyl acetate solution of THEICTA (total internal heat transfer coefficient) by mass percent under the protection of nitrogen, irradiating with an LED lamp with the wavelength of 365nm while monitoring the reaction by FTIR (FTIR), and removing the solvent by rotary evaporation to obtain a product C when the mercapto absorption peak in the reaction system disappears;
(4) And (3) heating the mixed solution B to 100 ℃, then adding a butyl acetate solution containing a product C and p-toluenesulfonic acid into the mixed solution B in a dropwise manner while stirring, monitoring the reaction through FTIR measurement, and carrying out vacuum rotary evaporation and drying on a reaction product after the carboxyl absorption peak in the reaction system disappears, thereby obtaining the modified acrylic resin, wherein the mass percentage of the product C in the butyl acetate is 30%, and the addition amount of the p-toluenesulfonic acid is 1% of the mass of the product C in the butyl acetate solution.
Comparative example 3 the same as example 1, except that the modified acrylate of comparative example 3 was prepared according to the following procedure:
(1) Mixing KH590, absolute ethyl alcohol and water in a three-neck flask according to a volume ratio of 3:1:5, regulating the pH value of the solution to be=5 by using glacial acetic acid, then heating the reaction system to 60 ℃, stirring and reacting for 2 hours under the protection of nitrogen, and then carrying out vacuum rotary evaporation and drying on the reaction product to obtain a solid product A with rich mercapto on the surface;
(2) Mixing a solid product A and toluene in a flask according to a mass ratio of 1:4, dropwise adding a photoinitiator 1173 while stirring, wherein the dropwise adding amount of the photoinitiator 1173 is 2% of the mass of the solid product A, then heating a reaction system to 50 ℃, dropwise adding a toluene solution with the mass percent of 4- (3-methyl-2-buten-2-yl) benzoic acid content of 20% into the reaction system under the protection of nitrogen, dropwise adding and stirring, irradiating with an LED lamp with a wavelength of 365nm, monitoring the reaction by FTIR measurement, and obtaining a mixed liquid B when a mercapto absorption peak in the reaction system disappears;
(3) Adding 10.8g of 3-mercapto-1, 2-propanediol into a flask, adding 1173 of 0.05g of photoinitiator and 70mL of toluene, stirring uniformly, then heating the flask to 50 ℃, dropwise adding ethoxylated trimethylolpropane triacrylate under the protection of nitrogen while stirring, irradiating with an LED lamp with the wavelength of 365nm, monitoring the reaction by FTIR measurement, and removing the solvent by rotary evaporation to obtain a product C when the mercapto absorption peak in the reaction system disappears;
(4) And (3) heating the mixed solution B to 100 ℃, then adding a butyl acetate solution containing a product C and p-toluenesulfonic acid into the mixed solution B in a dropwise manner while stirring, monitoring the reaction through FTIR measurement, and carrying out vacuum rotary evaporation and drying on a reaction product after the carboxyl absorption peak in the reaction system disappears, thereby obtaining the modified acrylic resin, wherein the mass percentage of the product C in the butyl acetate is 30%, and the addition amount of the p-toluenesulfonic acid is 1% of the mass of the product C in the butyl acetate solution.
Performance testing
Under the condition of avoiding light, the components of the invention examples 1-6 and the comparative examples 1-3 are respectively mixed and stirred uniformly according to the formula amount to obtain 8 kinds of printing inks, and the viscosity of the printing inks obtained in the examples 1-6 and the comparative examples 2-3 is within 30 mPas (25 ℃) and the viscosity of the printing ink obtained in the comparative example 1 is 80 mPas (25 ℃) after being tested, so that the requirement of ink-jet printing is not met, and the printing inks cannot be used for ink-jet printing.
The inks obtained in examples 1 to 6 and comparative examples 2 to 3 of the present invention were sprayed on the smooth PCB surface, respectively, with a photo-curing thickness of 20. Mu.m, and then the photo-curing ink coatings obtained in examples 1 to 6 and comparative examples 2 to 3 of the present invention were subjected to the relevant performance test, and the test results are shown in Table 1.
Viscosity test: the ink viscosity was measured at 25℃using a BROOKFIELD DV-II+Pro rotational viscometer.
Average particle diameter: the nano-particle size distribution of the ink was tested using a Zeta potential analyzer.
Surface tension: the surface tension of the ink was measured using a surface tensiometer.
Jet printing fluency and printing precision: and (3) adopting an ink-jet printer to spray and print solder resist ink on the etched copper-clad plate and performing ultraviolet curing, and observing the smoothness and printing precision of ink spray printing.
Thermal shock test: after 15 minutes at minus 35 ℃, the coating is transferred to 125 ℃ for 15 minutes, and the coating is circulated for 100 times, so as to observe whether cracks are generated on the surface of the coating.
Adhesion test: the test was performed according to QB/T4580-2013.
Hardness testing: the test was performed according to QB/T4580-2013.
Solder test: and (3) carrying out a 10-second soldering tin test on the copper-clad plate printed with the solder resist ink at 260 ℃ for three times, observing the situation, carrying out a 3M600# adhesive tape test again, and observing the ink falling-off situation.
Acid and alkali resistance test: the test was performed according to QB/T4580-2013.
TABLE 1
With the above-described preferred embodiments according to the present invention as an illustration, the above-described descriptions can be used by persons skilled in the relevant art to make various changes and modifications without departing from the scope of the technical idea of the present invention. The technical scope of the present invention is not limited to the description, but must be determined according to the scope of claims.
Claims (5)
1. The high-temperature-resistant UV ink-jet printing ink is characterized by comprising the following components in percentage by weight:
30-40% of modified acrylic ester
Pigment 5-10%
3-10% of photoinitiator
0.5 to 1 percent of dispersing agent
Acrylic ester monomer balance;
the preparation method of the modified acrylic ester comprises the following steps:
(1) Mixing KH590, ethanol and water in a volume ratio of 3:1:5 in a three-neck flask, regulating the pH of the solution to be 3-6 by glacial acetic acid, then heating the reaction system to 60 ℃, stirring under the protection of nitrogen for 2 hours, and performing vacuum rotary evaporation and drying on the reaction product to obtain a solid product A with rich mercapto on the surface;
(2) Mixing a solid product A and toluene in a flask according to a mass ratio of 1:4, dropwise adding a photoinitiator 1173 while stirring, wherein the dropwise adding amount of the photoinitiator 1173 is 2% of the mass of the solid product A, then heating a reaction system to 50 ℃, dropwise adding a toluene solution with the mass percent of 4- (3-methyl-2-buten-2-yl) benzoic acid content of 20% into the reaction system under the protection of nitrogen, dropwise adding and stirring, irradiating with an LED lamp with a wavelength of 365nm, monitoring the reaction by FTIR measurement, and obtaining a mixed liquid B when a mercapto absorption peak in the reaction system disappears;
(3) Adding 10.8g of 3-mercapto-1, 2-propanediol into a flask, adding 1173 g of photoinitiator and 70mL of toluene, stirring uniformly, then heating the flask to 50 ℃, dropwise adding 50% butyl acetate solution of THEICTA (total internal heat transfer coefficient) by mass percent under the protection of nitrogen, irradiating with an LED lamp with the wavelength of 365nm while monitoring the reaction by FTIR (FTIR), and removing the solvent by rotary evaporation to obtain a product C when the mercapto absorption peak in the reaction system disappears;
(4) Heating the mixed solution B to 100 ℃, then adding a butyl acetate solution containing a product C and p-toluenesulfonic acid into the mixed solution B in a dropwise manner while stirring, monitoring the reaction through FTIR measurement, and carrying out vacuum rotary evaporation and drying on the reaction product after the carboxyl absorption peak in the reaction system disappears to obtain modified acrylic ester, wherein the mass percentage of the product C in the butyl acetate is 30%, and the addition amount of the p-toluenesulfonic acid is 1% of the mass of the product C in the butyl acetate solution;
the acrylate monomer comprises at least one of pentaerythritol tetraacrylate, 1, 6-ethylene glycol diacrylate and tripropylene glycol diacrylate.
2. The high temperature resistant UV inkjet printing ink according to claim 1 wherein the pigment is a nano white paste.
3. The high temperature resistant UV inkjet printing ink according to claim 1 wherein the photoinitiator includes at least one of a photoinitiator 184, TPO, 1173, 819.
4. The high temperature resistant UV inkjet printing ink according to claim 1 wherein the dispersant includes at least one of a courtesy DP983, BYK168, dyheight 710.
5. A high temperature resistant UV inkjet printing ink according to any one of claims 1 to 4 wherein the method of preparation includes the steps of:
under the condition of avoiding light, the components are mixed and stirred uniformly according to the formula amount, and the product is obtained.
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| CN108786713A (en) * | 2018-06-08 | 2018-11-13 | 南京师范大学 | A kind of nano hydroxyapatite adsorbent and its preparation method and application that parents' absorbent-type is sulfhydryl modified |
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| CN108786713A (en) * | 2018-06-08 | 2018-11-13 | 南京师范大学 | A kind of nano hydroxyapatite adsorbent and its preparation method and application that parents' absorbent-type is sulfhydryl modified |
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| Title |
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| 一种巯基酯类光敏胶单体的合成及其性能研究;周艳阳;张秋禹;周健;刘清;;中国胶粘剂(05);第9-14页 * |
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