CN114921180B - Organic silicon modified epoxy resin gloss oil and preparation method thereof - Google Patents
Organic silicon modified epoxy resin gloss oil and preparation method thereof Download PDFInfo
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- CN114921180B CN114921180B CN202210121765.5A CN202210121765A CN114921180B CN 114921180 B CN114921180 B CN 114921180B CN 202210121765 A CN202210121765 A CN 202210121765A CN 114921180 B CN114921180 B CN 114921180B
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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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
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Abstract
The invention relates to the technical field of UV gloss oil, in particular to organic silicon modified epoxy resin gloss oil and a preparation method thereof. When the chip is exposed in humid air, a thick water molecule film is formed on the surface of the chip, and the appearance of the water molecule film can reduce the surface Insulation Resistance (IR) of the circuit board and easily cause local corrosion and micropore corrosion, so that the transmission performance of the electric signals of the circuit board is deteriorated. Based on the problems, the invention provides the organic silicon modified epoxy resin gloss oil, the hydroxyl-terminated methyl vinyl silicone oil is used as the water-based UV resin to introduce organic silicon oxygen bonds, the existence of the organic silicon oxygen bonds reduces the surface tension of the gloss oil cured coating, the hydrophobic property of the gloss oil cured coating is obviously improved, the protective coating has insulating and waterproof effects, and the use reliability of a chip can be ensured.
Description
Technical Field
The invention relates to the technical field of UV gloss oil, in particular to organic silicon modified epoxy resin gloss oil and a preparation method thereof.
Background
When the chip is exposed in humid air, a thick water molecular film is formed on the surface of the chip, the occurrence of the water molecular film can reduce the surface Insulation Resistance (IR) of the circuit board and easily cause local corrosion and micropore corrosion, so that the transmission performance of the circuit board electrical signals is deteriorated, and the more serious consequence is that crosstalk, electrical leakage and transmission interruption are caused, and further permanent signal interruption, namely short circuit, can be caused.
The application of an insulating, waterproof protective coating on the chip surface can be a practical, economical and practical method for improving the reliability of chip products. The existence of the protective coating can ensure that the chip can be applied in the environment with more severe conditions such as underwater, aerospace, military and the like.
Disclosure of Invention
Aiming at the problems in the prior art, the technical problems to be solved by the invention are as follows: when the chip is exposed in humid air, a thick water molecule film is formed on the surface of the chip, and the appearance of the water molecule film can reduce the surface Insulation Resistance (IR) of the circuit board and easily cause local corrosion and micropore corrosion, so that the transmission performance of the electric signals of the circuit board is deteriorated.
The technical scheme adopted by the invention for solving the technical problems is as follows: the invention provides organic silicon modified epoxy resin gloss oil which comprises the following components in parts by weight:
specifically, the aqueous UV resin is prepared according to the following steps:
(1) The hydroxyl in the hydroxyl silicone oil and the secondary hydroxyl in the epoxy resin are subjected to graft reaction, and an organic silicon-oxygen bond is introduced into the structure of the epoxy resin
120g E51 epoxy resin and 350g excess hydroxyl-terminated methyl vinyl silicone oil (trade name: MY 1203V) are mixed evenly, 1.5g dibutyltin dilaurate is added for mixing and stirring evenly, the mixture is stirred and reacted at 120 ℃ until the hydroxyl absorption peak in the system does not change any more, and the excess hydroxyl-terminated methyl vinyl silicone oil is removed through reduced pressure distillation, so that the organic silicon modified epoxy resin is obtained;
(2) The epoxy group in the organic silicon modified epoxy resin reacts with the carboxyl group in the 3- (phenylthio) acrylic acid to introduce a photopolymerization double bond
Adding 0.1g of polymerization inhibitor p-hydroxyanisole into the organosilicon modified epoxy resin reaction system in the step (1), stirring and heating to 75 ℃, adding 110g of 3- (phenylthio) acrylic acid and 1.2g of initiator N, N-dimethylbenzylamine, dropwise adding within 0.5-1h, heating the reaction system to 85 ℃, reacting at constant temperature until the acid value of the system is lower than 3mgKOH/g, and finishing the reaction to obtain the sulfur-containing organosilicon modified epoxy acrylate;
(3) Hydroxyl in the sulfur-containing organic silicon modified epoxy acrylate reacts with anhydride group to introduce carboxyl hydrophilic group
And (3) reducing the temperature of the sulfur-containing organosilicon modified epoxy acrylate system in the step (2) to 65 ℃, adding 40g of maleic anhydride, 2g of tetrabutylammonium bromide and 0.15g of p-hydroxyanisole, fully stirring and uniformly mixing, reacting at constant temperature until the content of the system is lower than 3mgKOH/g, finishing the reaction, and adding water for diluting to obtain the water-based UV resin with the solid content of 60%.
Specifically, the polymerized monomer is ethoxylated trimethylolpropane triacrylate, ethoxylated pentaerythritol tetraacrylate or polyethylene glycol (600) diacrylate.
Specifically, the photoinitiator is (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide, ethyl 2,4, 6-trimethylbenzoylphenylphosphonate or phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide.
Specifically, the leveling agent is a water-based organic silicon leveling agent.
Specifically, the water-based organic silicon flatting agent is one or more of Dow Corning DC-27, digao TEGO Glide A115, BYK333 and DH-4033.
Specifically, the defoaming agent is an organic silicon defoaming agent or a polyether defoaming agent.
Specifically, the organic silicon defoamer is one or more of BYK-024, BYK-019, digao 805 defoamer and Dow Corning DC-65.
Specifically, the polyether type defoaming agent is Dow Corning defoaming agent AFE-1410 or digao
Foamex1488。
Specifically, the neutralizing agent is triethanolamine, triethylamine, ammonium dihydrogen phosphate or ammonia water.
The invention has the beneficial effects that:
(1) According to the invention, the hydroxyl-terminated methyl vinyl silicone oil is used as the water-based UV resin to introduce organic silicon oxygen bonds, and the hydroxyl groups at two ends of each hydroxyl-terminated methyl vinyl silicone oil molecule respectively perform a grafting reaction with secondary hydroxyl groups in two epoxy resin molecular structures, so that two ends of each hydroxyl-terminated methyl vinyl silicone oil molecule are respectively connected with one epoxy resin molecule after the reaction, the surface tension of the gloss oil curing coating is reduced due to the existence of the organic silicon oxygen bonds, and the hydrophobic property of the gloss oil curing coating is obviously improved;
(2) The hydroxyl-terminated methyl vinyl silicone oil also contains polymerizable double bonds in the molecular structure, can participate in the photocuring reaction, and has good effects on improving the compactness of a gloss oil cured coating and improving the corrosion resistance of the coating;
(3) In addition, the 3- (phenylthio) acrylic acid and epoxy groups at two ends of the epoxy resin generate ring-opening reaction, benzene ring structures are introduced at two ends of the epoxy resin, the benzene rings are distributed at two ends and the middle of the resin, and the benzene rings distributed in a staggered manner have a good pi-pi conjugated effect, so that the whole aqueous UV resin structure is more stable, the obtained varnish cured coating is more compact, and the improvement of the corrosion resistance of varnish is more favorable.
Detailed Description
The present invention will now be described in further detail with reference to examples.
The aqueous UV resins of the following examples of the invention were prepared according to the following steps:
(1) The hydroxyl in the hydroxyl silicone oil and the secondary hydroxyl in the epoxy resin are subjected to graft reaction, and an organic silicon-oxygen bond is introduced into the structure of the epoxy resin
120g of E51 epoxy resin and 350g of excessive hydroxyl-terminated methyl vinyl silicone oil (brand: MY 1203V) are uniformly mixed, 1.5g of dibutyltin dilaurate is added for uniform mixing and stirring, the mixture is stirred and reacted at 120 ℃ until the hydroxyl absorption peak in the system does not change any more, and the excessive hydroxyl-terminated methyl vinyl silicone oil is removed by reduced pressure distillation to obtain the organic silicon modified epoxy resin;
(2) The epoxy group in the organic silicon modified epoxy resin reacts with the carboxyl group in the 3- (phenylthio) acrylic acid to introduce a photopolymerization double bond
Adding 0.1g of polymerization inhibitor p-hydroxyanisole into the organosilicon modified epoxy resin reaction system in the step (1), stirring and heating to 75 ℃, adding 110g of 3- (phenylthio) acrylic acid and 1.2g of initiator N, N-dimethylbenzylamine, dropwise adding within 50min, heating the reaction system to 85 ℃, reacting at constant temperature until the acid value of the system is lower than 3mgKOH/g, and finishing the reaction to obtain the sulfur-containing organosilicon modified epoxy acrylate;
(3) Carboxyl hydrophilic group is introduced by the reaction of hydroxyl in the sulfur-containing organic silicon modified epoxy acrylate and anhydride group
And (3) reducing the temperature of the sulfur-containing organosilicon modified epoxy acrylate system in the step (2) to 65 ℃, adding 40g of maleic anhydride, 2g of tetrabutylammonium bromide and 0.15g of p-hydroxyanisole, fully stirring and uniformly mixing, reacting at constant temperature until the content of the system is lower than 3mgKOH/g, finishing the reaction, and adding water for diluting to obtain the water-based UV resin with the solid content of 60%.
The polymerized monomer used in the following examples of the present invention was ethoxylated trimethylol triacrylate, ethoxylated pentaerythritol tetraacrylate or polyethylene glycol (600) diacrylate.
The photoinitiators in the following examples of the invention are (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide, ethyl 2,4, 6-trimethylbenzoylphenylphosphonate or phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide.
The aqueous organosilicon leveling agent adopted in the following embodiments of the invention is Dow Corning DC-27, digao TEGO Glide A115, BYK333 or DH-4033.
The silicone antifoam agents employed in the following examples of the invention are BYK-024, BYK-019, dow Corning 805 antifoam, dow Corning DC-65, dow Corning antifoam AFE-1410 or Diw
Foamex1488。
The neutralizing agent used in the following examples of the present invention is triethanolamine, triethylamine, ammonium dihydrogen phosphate or ammonia water.
Example 1
The organic silicon modified epoxy resin gloss oil comprises the following components in parts by weight:
example 2
The organic silicon modified epoxy resin gloss oil comprises the following components in parts by weight:
example 3
The organic silicon modified epoxy resin gloss oil comprises the following components in parts by weight:
example 4
The organic silicon modified epoxy resin gloss oil comprises the following components in parts by weight:
example 5
The organic silicon modified epoxy resin gloss oil comprises the following components in parts by weight:
example 6
The organic silicon modified epoxy resin gloss oil comprises the following components in parts by weight:
comparative example 1 the same as example 1 except that the aqueous UV resin used in comparative example 1 was prepared according to the following procedure:
(1) The hydroxyl in the hydroxyl silicone oil and the secondary hydroxyl in the epoxy resin are subjected to grafting reaction, and an organic silicon oxygen bond is introduced into the structure of the epoxy resin
120g of E51 epoxy resin and 1800g of excessive alcoholic hydroxyl single-end-capped long-chain alkyl silicone oil (the trade name is MY 8861) are uniformly mixed, 1.5g of dibutyltin dilaurate is added for uniform mixing and stirring, the mixture is stirred and reacted at the temperature of 120 ℃ until the hydroxyl absorption peak in the system does not change any more, and the excessive alcoholic hydroxyl single-end-capped long-chain alkyl silicone oil is removed by reduced pressure distillation to obtain organic silicon modified epoxy resin;
(2) The epoxy group in the organic silicon modified epoxy resin reacts with the carboxyl group in the 3- (phenylthio) acrylic acid to introduce a photopolymerization double bond
Adding 0.1g of polymerization inhibitor p-hydroxyanisole into the organosilicon modified epoxy resin reaction system in the step (1), stirring and heating to 75 ℃, adding 110g of 3- (phenylthio) acrylic acid and 1.2g of initiator N, N-dimethylbenzylamine, dropwise adding within 50min, heating the reaction system to 85 ℃, reacting at constant temperature until the acid value of the system is lower than 3mgKOH/g, and finishing the reaction to obtain the sulfur-containing organosilicon modified epoxy acrylate;
(3) Hydroxyl in the sulfur-containing organic silicon modified epoxy acrylate reacts with anhydride group to introduce carboxyl hydrophilic group
And (3) reducing the temperature of the sulfur-containing organosilicon modified epoxy acrylate system in the step (2) to 65 ℃, adding 40g of maleic anhydride, 2g of tetrabutylammonium bromide and 0.15g of p-hydroxyanisole, fully stirring and uniformly mixing, reacting at constant temperature until the content of the system is lower than 3mgKOH/g, finishing the reaction, and adding water for diluting to obtain the water-based UV resin with the solid content of 60%.
Comparative example 2 the same as example 1 except that the aqueous UV resin used in comparative example 2 was prepared according to the following procedure:
(1) The hydroxyl in the hydroxyl silicone oil and the secondary hydroxyl in the epoxy resin are subjected to graft reaction, and an organic silicon-oxygen bond is introduced into the structure of the epoxy resin
120g of E51 epoxy resin and 350g of excessive hydroxyl-terminated methyl vinyl silicone oil (brand: MY 1203V) are uniformly mixed, 1.5g of dibutyltin dilaurate is added for uniform mixing and stirring, the mixture is stirred and reacted at 120 ℃ until the hydroxyl absorption peak in the system does not change any more, and the excessive hydroxyl-terminated methyl vinyl silicone oil is removed by reduced pressure distillation to obtain the organic silicon modified epoxy resin;
(2) The epoxy group in the organic silicon modified epoxy resin reacts with the carboxyl group in the 2-phenyl acrylic acid to introduce a photopolymerization double bond
Adding 0.1g of polymerization inhibitor p-hydroxyanisole into the organosilicon modified epoxy resin reaction system in the step (1), stirring and heating to 75 ℃, adding 90.5g of 2-phenylacrylic acid and 1.2g of initiator N, N-dimethylbenzylamine, dropwise adding within 50min, heating the temperature of the reaction system to 85 ℃, reacting at constant temperature until the acid value of the system is lower than 3mgKOH/g, and finishing the reaction to obtain the sulfur-containing organosilicon modified epoxy acrylate;
(3) Carboxyl hydrophilic group is introduced by the reaction of hydroxyl in the sulfur-containing organic silicon modified epoxy acrylate and anhydride group
And (3) reducing the temperature of the sulfur-containing organosilicon modified epoxy acrylate system in the step (2) to 65 ℃, adding 40g of maleic anhydride, 2g of tetrabutylammonium bromide and 0.15g of p-hydroxyanisole, fully stirring and uniformly mixing, reacting at constant temperature until the content of the system is lower than 3mgKOH/g, finishing the reaction, and adding water for diluting to obtain the water-based UV resin with the solid content of 60%.
And (3) performance testing:
the organosilicon modified epoxy resin gloss oil obtained in examples 1-6 and comparative examples 1-2 is coated on the surface of a chip and photocured, and then a related performance test is carried out, wherein the thickness of the test coating is 5 μm, and the specific test results are shown in table 1:
neutral salt spray resistance test: the tests were carried out according to the determination of the neutral salt spray resistance of the paints and varnishes of the standard GB/T1771-2007.
Electrical insulation: the tests were carried out according to the standard HG/T3330-2012 insulating paint film breakdown strength test.
Thermal shock resistance; the test is carried out by referring to 6.4.14 temperature change resistance in HG/T4570-2013 automobile water-based paint, and the automobile water-based paint is placed in a low temperature box for 12 hours at the temperature of 60 ℃ below zero, then placed in a high temperature box for 12 hours at the temperature of 300 ℃ and repeated for 100 times.
Weather resistance: the tests were carried out according to standard GB/T1865-2009 colour lacquers and varnishes artificial weathering and artificial radiation exposure filtered xenon arc radiation medium cycle A.
Mildew resistance: the test was carried out according to the standard GB/T1741-2007 paint film resistance assay.
TABLE 1
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (9)
1. The organic silicon modified epoxy resin gloss oil is characterized by comprising the following components in parts by weight:
60-80 parts of water-based UV resin
10-15 parts of polymerized monomer
3-5 parts of photoinitiator
1-3 parts of flatting agent
1-2 parts of defoaming agent
1-2 parts of neutralizing agent
10-20 parts of water;
the aqueous UV resin is prepared according to the following steps:
(1) The hydroxyl in the hydroxyl silicone oil and the secondary hydroxyl in the epoxy resin are subjected to graft reaction, and an organic silicon-oxygen bond is introduced into the structure of the epoxy resin
120g of E51 epoxy resin and 350g of excessive hydroxyl-terminated methyl vinyl silicone oil are uniformly mixed, 1.5g of dibutyltin dilaurate is added for uniform mixing and stirring, the mixture is stirred and reacted at the temperature of 120 ℃ until the hydroxyl absorption peak in the system does not change any more, and the excessive hydroxyl-terminated methyl vinyl silicone oil is removed by reduced pressure distillation to obtain the organic silicon modified epoxy resin;
(2) The epoxy group in the organic silicon modified epoxy resin reacts with the carboxyl group in the 3- (phenylthio) acrylic acid to introduce a photopolymerization double bond
Adding 0.1g of polymerization inhibitor p-hydroxyanisole into the organosilicon modified epoxy resin reaction system in the step (1), stirring and heating to 75 ℃, adding 110g of 3- (phenylthio) acrylic acid and 1.2g of initiator N, N-dimethylbenzylamine, dropwise adding within 0.5-1h, heating the reaction system to 85 ℃, reacting at constant temperature until the acid value of the system is lower than 3mgKOH/g, and finishing the reaction to obtain the sulfur-containing organosilicon modified epoxy acrylate;
(3) Carboxyl hydrophilic group is introduced by the reaction of hydroxyl in the sulfur-containing organic silicon modified epoxy acrylate and anhydride group
And (3) reducing the temperature of the sulfur-containing organosilicon modified epoxy acrylate system in the step (2) to 65 ℃, adding 40g of maleic anhydride, 2g of tetrabutylammonium bromide and 0.15g of p-hydroxyanisole, fully stirring and uniformly mixing, reacting at constant temperature until the content of the system is lower than 3mgKOH/g, ending the reaction, and adding water for diluting to obtain the water-based UV resin with the solid content of 60%.
2. The silicone-modified epoxy resin gloss oil of claim 1, wherein the polymeric monomer is ethoxy pentaerythritol tetraacrylate, polyethylene glycol 600 diacrylate.
3. The silicone-modified epoxy resin varnish according to claim 1, wherein the photoinitiator is (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide, ethyl 2,4, 6-trimethylbenzoylphenylphosphonate, or phenyl bis (2, 4, 6-trimethylbenzoyl) phosphine oxide.
4. The silicone-modified epoxy resin gloss oil of claim 1, wherein the leveling agent is an aqueous silicone leveling agent.
5. The silicone modified epoxy resin gloss oil of claim 4, wherein the aqueous silicone leveling agent is one or more of Dow Corning DC-27, digao TEGO Glide A115, BYK333, and DH-4033.
6. The silicone-modified epoxy resin gloss oil of claim 1, wherein the defoamer is a silicone defoamer or a polyether defoamer.
7. The silicone modified epoxy resin gloss oil of claim 6, wherein the silicone defoamer is one or more of BYK-024, BYK-019, digao 805 defoamer, dow Corning DC-65.
8. The silicone modified epoxy resin gloss oil of claim 6, wherein the polyether defoamer is Digao TEGO Foamex1488.
9. The silicone-modified epoxy resin gloss oil of claim 1, wherein the neutralizing agent is triethanolamine, triethylamine, ammonium dihydrogen phosphate or ammonia water.
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| CN101974143B (en) * | 2010-10-14 | 2012-07-18 | 华南理工大学 | Organic silicon modified epoxy acrylate aqueous dispersion and preparation method thereof |
| CN104263208A (en) * | 2014-10-24 | 2015-01-07 | 崇州市美涂士涂料科技有限公司 | UV (Ultraviolet) laminated topcoat gloss coating with performances of smell removal, stain resistance and yellowing resistance as well as preparation method and construction process thereof |
| CN104761994B (en) * | 2015-04-10 | 2016-11-23 | 南昌航空大学 | A kind of preparation method of photo-curable silicone modified epoxy paint film |
| CN105348998A (en) * | 2015-11-12 | 2016-02-24 | 三棵树涂料股份有限公司 | Organosilicon modified waterborne photo-curing epoxy-acrylic coating and preparation method thereof |
| CN111349377B (en) * | 2020-04-28 | 2021-10-19 | 中科院广州化学有限公司 | Organic silicon modified waterborne epoxy acrylate UV curing coating and preparation and application thereof |
| CN113321990A (en) * | 2021-06-22 | 2021-08-31 | 广东鑫皇冠新材料有限公司 | Ultraviolet curing coating and preparation method thereof |
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