CN114621614A - Photocureable coating and preparation method thereof - Google Patents
Photocureable coating and preparation method thereof Download PDFInfo
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- CN114621614A CN114621614A CN202111297279.0A CN202111297279A CN114621614A CN 114621614 A CN114621614 A CN 114621614A CN 202111297279 A CN202111297279 A CN 202111297279A CN 114621614 A CN114621614 A CN 114621614A
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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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
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Abstract
The invention belongs to the technical field of C09D175/14 coatings, and particularly relates to a photocureable coating and a preparation method thereof. A photocureable coating is prepared from the following raw materials: polyester polyol, polyisocyanate, acrylate monomers, a catalyst, a reactive diluent, a photoinitiator and an auxiliary agent. The photocureable coating prepared by the invention is used for electronic products, and can be used for sealing and bonding circuit boards and parts of the electronic products; the photocureable coating prepared by the method has good adhesive force and corrosion resistance, and the application period in the field of electronic products is prolonged; the photocureable coating prepared by the method has better toughness and impact resistance, and ensures the safety of application in the field of electronic products.
Description
Technical Field
The invention belongs to the technical field of coatings, and particularly relates to a photocureable coating and a preparation method thereof.
Background
The existence of coatings is not unknown to people, and the conventional coatings generally remove the solvent in the coating by heating or physical drying to obtain a cured paint film, but with the development of technology, along with the optimization of the process and the improvement of the raw materials for preparing the product, more and more photocuring coatings are used at present.
However, the ultraviolet light curing coating composition is prepared by polyurethane acrylic acid oligomer and biological monomer, wherein the biological monomer can be acrylic acid monomer, and the substance extracted from animals and plants is used for preparing the ultraviolet light curing coating composition.
With the improvement of national environmental protection requirements and the improvement of coating performance requirements of consumers, the development of a photocuring coating which is environment-friendly, safe and long in service life is an important problem in the present stage.
Disclosure of Invention
In order to solve the above technical problems, a first aspect of the present invention provides a photocurable coating, which is prepared from the following raw materials: polyester polyol, polyisocyanate, acrylate monomers, a catalyst, a reactive diluent, a photoinitiator and an auxiliary agent.
In some preferred embodiments, the polyisocyanate is selected from at least one of TMHDI, HDI, HTDI, MDI, IPDI, HMDI, TDI.
In some preferred embodiments, the polyisocyanate is IPDI.
IPDI, an alicyclic diisocyanate, named isophorone diisocyanate, CAS: 4098-71-9.
In some preferred embodiments, the acrylate monomer is at least one selected from the group consisting of acrylate, methacrylate, hydroxyethyl methacrylate, and butyl acrylate.
More preferably, the acrylate monomers are hydroxyethyl methacrylate and methacrylate.
In some preferred embodiments, the weight ratio of hydroxyethyl methacrylate to methacrylate is 1: (0.3-0.7).
More preferably, the weight ratio of the hydroxyethyl methacrylate to the methacrylate is 1: 0.6.
during the experiments the applicant found that the proportions of hydroxyethyl methacrylate and methacrylate added in the present system had a major effect on the properties of the coatings prepared, and the applicant speculated that this occurred because: in the system, with the addition of hydroxyethyl methacrylate and methacrylate, acrylate groups and methacrylate groups containing hydroxyl groups can be provided in the system, and new crosslinking effect can be formed between the acrylate groups and the methacrylate groups and the polyol and the polyisocyanate, and when the acrylate groups and the methacrylate groups exist in the system, the phenomenon of shrinkage during photocuring can be avoided.
In addition, the applicant finds that the weight ratio of the hydroxyethyl methacrylate to the methacrylate also affects the stability of the system, and when the content of the hydroxyethyl methacrylate in the system is too high, the application performance of the prepared coating is reduced, and internal defects are easily caused during coating application; however, when the content of the methacrylate is too high, the interaction strength between the active substances of the system is affected, and the paint film is shrunk in the photocuring process of the paint.
In some preferred embodiments, the reactive diluent is selected from one or more of acrylate reactive diluents, vinyl reactive diluents, and epoxy reactive diluents.
In some preferred embodiments, the reactive diluent is an acrylate reactive diluent.
In some preferred embodiments, the acrylate reactive diluent is selected from at least one of 1, 6-hexanediol diacrylate, dipropylene glycol diacrylate, hydroxypropyl methacrylate, triethylene glycol dimethacrylate, lauryl acrylate, ethoxyethyl acrylate, trimethylolpropane triacrylate, diethylene glycol diacrylate, trimethylolpropane triacrylate.
In some preferred embodiments, the acrylate reactive diluent is 1, 6-hexanediol diacrylate and trimethylolpropane triacrylate, in a weight ratio of 7: 3-9: 1.
in some preferred embodiments, the weight ratio of 1, 6-hexanediol diacrylate to trimethylolpropane triacrylate is 8: 2.
in the experimental process, the applicant finds that the type of the selected reactive diluent has a great influence on the adhesion and the impact resistance of the prepared coating, and in the application, the applicant finds that, through a great amount of creative experiments, when 1, 6-hexanediol diacrylate and trimethylolpropane triacrylate are used as the reactive diluents, the adhesion of the prepared coating on the surface of a PCB can reach 0 grade and the impact resistance is greatly improved, and the applicant speculates that the reason for the phenomenon is that: when 1, 6-hexanediol diacrylate and trimethylolpropane triacrylate are used in the system, free radicals are generated in the system when light curing occurs, and the reaction activity of the system is greatly improved due to the existence of active hydroxyl groups and other groups in the 1, 6-hexanediol diacrylate and the trimethylolpropane triacrylate, but the applicant finds that the viscosity of the system is increased to a certain extent due to the addition of the trimethylolpropane triacrylate, and a certain hindering effect is provided for the reaction between reactants, but in the system, the weight ratio of the 1, 6-hexanediol diacrylate to the trimethylolpropane triacrylate is controlled to be 8: 2, the problem of overlarge system viscosity can be solved, so that the contact frequency between active groups is promoted, the intermolecular van der waals force and hydrogen bond interaction are promoted, and the adhesive force of the active groups on a PCB (printed circuit board) is enhanced.
Meanwhile, when the PCB is acted by the outside, the impact of external force can be counteracted through strong intermolecular interaction, and the falling of a paint film or the damage of the PCB caused by the impact of the external force is slowed down.
In some preferred embodiments, the weight of the acrylate based active agent is 40 to 70wt% of the weight of the acrylate based monomer.
In the experimental process, the applicant finds that the addition amount of the acrylate reactive diluent needs to be specially controlled, and when the content of the added acrylate reactive diluent is more than 70wt% of the weight of the acrylate monomer, the pinhole phenomenon occurs when the coating is used; however, when the amount of the reactive diluent added is less than 40wt% based on the weight of the acrylate monomer, the dilution effect is greatly reduced, and the performance of the coating is affected.
In some preferred embodiments, the catalyst is stannous octoate.
In some preferred embodiments, the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-propanone.
2-hydroxy-2-methyl-1-phenyl-1-propanone, the structural formula is:
。
in some preferred embodiments, the auxiliary agent comprises at least one of an accelerator, a color paste, a color developer, an antioxidant, an ultraviolet absorber, a filler and a coupling agent.
In some preferred embodiments, the auxiliaries include antioxidants, fillers and coupling agents.
In some preferred embodiments, the antioxidant is antioxidant 1010.
In some preferred embodiments, the filler is at least one of zinc oxide and aluminum oxide.
In some preferred embodiments, the coupling agent is vinyltriethoxysilane.
In some preferred embodiments, the polyester polyol is an aliphatic polyester polyol and/or an aromatic polyester polyol.
In some preferred embodiments, the polyester polyol is selected from at least one of an adipic acid-ethylene glycol-1, 4-butanediol polyester polyol, an adipic acid-neopentyl glycol polyester polyol, an adipic acid-1, 6-hexanediol polyester polyol, an adipic acid-terephthalic acid-phthalic anhydride-diethylene glycol polyester polyol, and an adipic acid-terephthalic anhydride-diethylene glycol polyester polyol.
In some preferred embodiments, the polyester polyol is an adipic acid-1, 4-butanediol polyester polyol.
In some preferred embodiments, the adipic acid-1, 4-butanediol polyester polyol has a hydroxyl value of 36 to 40 mgKOH/g.
In some preferred embodiments, the polyester polyol has an average molecular weight of 2000-.
More preferably, the adipic acid-1, 4-butanediol polyester polyol has an average molecular weight of 3000.
Adipic acid-1, 4-butanediol polyester polyol, type PE-2811, was purchased from Huafeng group.
During the experiment, the applicant finds that the average molecular weight of the adipic acid-1, 4-butanediol polyester polyol in the system is different, and the performance of the prepared coating is also greatly different, when the average molecular weight of the adipic acid-1, 4-butanediol polyester polyol is 3000, the reaction between the adipic acid-1, 4-butanediol polyester polyol and polyisocyanate in the system can further generate polyurethane, and the toughness of the prepared coating can be changed through the control of the polyester polyol with specific molecular weight, and the applicant speculates that the phenomenon occurs because: in the system, the polyether glycol with the average molecular weight of 3000 can ensure the reaction of active hydroxyl and isocyanate in the system, avoid the reaction with a photoinitiator in the reaction process, avoid the grafting reaction, ensure the regularity of a formed network structure and improve the toughness of the prepared coating.
In some preferred embodiments, the preparation raw materials comprise, by weight: 10-20 parts of polyester polyol, 15-30 parts of polyisocyanate, 5-8 parts of acrylate monomer, 0.01-0.1 part of catalyst, 2-5.6 parts of reactive diluent, 0.1-3 parts of photoinitiator, 2-5 parts of filler, 0.5-1 part of coupling agent and 0.5-2 parts of antioxidant.
The second aspect of the present invention provides a method for preparing a photocurable coating, comprising the steps of:
mixing the prepared raw materials, stirring, and obtaining the photocureable coating at the temperature of 30-70 ℃.
Has the advantages that: the photocureable coating prepared by the invention has the following advantages:
1. the photocureable coating prepared by the invention is used for electronic products, and can be used for sealing and bonding circuit boards and parts of the electronic products;
2. the photocureable coating prepared by the method has good adhesive force and corrosion resistance, and the application period in the field of electronic products is prolonged;
3. the photocureable coating prepared by the method has better toughness and impact resistance, and ensures the safety of application in the field of electronic products.
Detailed Description
Examples
Example 1
The photocureable coating comprises the following preparation raw materials in parts by weight: 12 parts of polyester polyol, 16 parts of polyisocyanate, 6 parts of acrylate monomer, 0.05 part of catalyst, 3 parts of reactive diluent, 1.2 parts of photoinitiator, 3 parts of filler, 0.7 part of coupling agent and 1 part of antioxidant.
The polyester polyol is adipic acid-1, 4-butanediol polyester polyol;
the hydroxyl value of the adipic acid-1, 4-butanediol polyester polyol is 36-40mgKOH/g, and the average molecular weight is 3000.
Adipic acid-1, 4-butanediol polyester polyol, type PE-2811, was purchased from Huafeng group.
The polyisocyanate is IPDI, CAS: 4098-71-9.
The acrylic ester monomer is hydroxyethyl methacrylate and methacrylic ester, and the weight ratio of the acrylic ester monomer to the methacrylic ester monomer is 1: 0.6.
the catalyst is stannous octoate.
The active diluent is 1, 6-hexanediol diacrylate and trimethylolpropane triacrylate, and the weight ratio of the active diluent is 8: 2.
the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone, and the structural formula is as follows:
。
the filler is alumina;
the coupling agent is vinyl triethoxysilane.
The antioxidant is 1010.
A preparation method of a photocureable coating comprises the following steps:
mixing the prepared raw materials, stirring, and obtaining the photocureable coating at 40 ℃.
Example 2
The photocureable coating comprises the following preparation raw materials in parts by weight: 12 parts of polyester polyol, 16 parts of polyisocyanate, 6 parts of acrylate monomer, 0.05 part of catalyst, 3 parts of reactive diluent, 1.2 parts of photoinitiator, 3 parts of filler, 0.7 part of coupling agent and 1 part of antioxidant.
The polyester polyol is adipic acid-1, 4-butanediol polyester polyol;
the hydroxyl value of the adipic acid-1, 4-butanediol polyester polyol is 36-40mgKOH/g, and the average molecular weight is 3000.
Adipic acid-1, 4-butanediol polyester polyol, type PE-2811, was purchased from Huafeng group.
The polyisocyanate is IPDI, CAS: 4098-71-9.
The acrylic ester monomer is hydroxyethyl methacrylate and methacrylic ester, and the weight ratio of the acrylic ester monomer to the methacrylic ester monomer is 1: 0.6.
the catalyst is stannous octoate.
The active diluent is 1, 6-hexanediol diacrylate.
The photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone, and the structural formula is as follows:
。
the filler is alumina;
the coupling agent is vinyl triethoxysilane.
The antioxidant is antioxidant 1010.
A method for preparing a photocurable coating material is described in example 1.
Example 3
The photocureable coating comprises the following preparation raw materials in parts by weight: 12 parts of polyester polyol, 16 parts of polyisocyanate, 6 parts of acrylate monomer, 0.05 part of catalyst, 3 parts of reactive diluent, 1.2 parts of photoinitiator, 3 parts of filler, 0.7 part of coupling agent and 1 part of antioxidant.
The polyester polyol is adipic acid-1, 4-butanediol polyester polyol;
the hydroxyl value of the adipic acid-1, 4-butanediol polyester polyol is 36-40mgKOH/g, and the average molecular weight is 3000.
Adipic acid-1, 4-butanediol polyester polyol, type PE-2811, was purchased from Huafeng group.
The polyisocyanate is IPDI, CAS: 4098-71-9.
The acrylic ester monomer is hydroxyethyl methacrylate and methacrylic ester, and the weight ratio of the acrylic ester monomer to the methacrylic ester monomer is 1: 0.6.
the catalyst is stannous octoate.
The active diluent is trimethylolpropane triacrylate.
The photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone, and the structural formula is as follows:
。
the filler is alumina;
the coupling agent is vinyl triethoxysilane.
The antioxidant is 1010.
A method for preparing a photocurable coating material is described in example 1.
Example 4
The photocureable coating comprises the following preparation raw materials in parts by weight: 12 parts of polyester polyol, 16 parts of polyisocyanate, 6 parts of acrylate monomer, 0.05 part of catalyst, 6 parts of reactive diluent, 1.2 parts of photoinitiator, 3 parts of filler, 0.7 part of coupling agent and 1 part of antioxidant.
The polyester polyol is adipic acid-1, 4-butanediol polyester polyol;
the hydroxyl value of the adipic acid-1, 4-butanediol polyester polyol is 36-40mgKOH/g, and the average molecular weight is 3000.
Adipic acid-1, 4-butanediol polyester polyol, type PE-2811, was purchased from Huafeng group.
The polyisocyanate is IPDI, CAS: 4098-71-9.
The acrylic ester monomer is hydroxyethyl methacrylate and methacrylic ester, and the weight ratio of the acrylic ester monomer to the methacrylic ester monomer is 1: 0.6.
the catalyst is stannous octoate.
The active diluent is 1, 6-hexanediol diacrylate and trimethylolpropane triacrylate, and the weight ratio of the active diluent is 8: 2.
the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone, and the structural formula is as follows:
。
the filler is alumina;
the coupling agent is vinyl triethoxysilane.
The antioxidant is antioxidant 1010.
A method for preparing a photocurable coating material is described in example 1.
Example 5
The photocureable coating comprises the following preparation raw materials in parts by weight: 12 parts of polyester polyol, 16 parts of polyisocyanate, 6 parts of acrylate monomer, 0.05 part of catalyst, 3 parts of reactive diluent, 1.2 parts of photoinitiator, 3 parts of filler, 0.7 part of coupling agent and 1 part of antioxidant.
The polyester polyol is adipic acid-hexanediol-1, 4-butanediol polyester polyol;
the hydroxyl value of the adipic acid-hexanediol-1, 4-butanediol polyester polyol is 53-59mgKOH/g, and the average molecular weight is 2000.
Adipate-hexanediol-1, 4-butanediol polyester polyol, type PE-1320, available from Huafeng group.
The polyisocyanate is IPDI, CAS: 4098-71-9.
The acrylic ester monomer is hydroxyethyl methacrylate and methacrylic ester, and the weight ratio of the acrylic ester monomer to the methacrylic ester monomer is 1: 0.6.
the catalyst is stannous octoate.
The active diluent is 1, 6-hexanediol diacrylate and trimethylolpropane triacrylate, and the weight ratio of the active diluent is 8: 2.
the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone, and the structural formula is as follows:
。
the filler is alumina;
the coupling agent is vinyl triethoxysilane.
The antioxidant is antioxidant 1010.
A method for preparing a photocurable coating material is described in example 1.
Example 6
A photo-curable coating material, whose embodiment is the same as example 1, is different from example 1 in that the weight ratio of hydroxyethyl methacrylate to methacrylate is 1: 1.
example 7
The specific implementation mode of the photo-curing coating is the same as that of example 1, and the difference from example 1 is that the reactive diluent is epoxy resin reactive diluent 660 purchased from medium petrochemical industry.
And (3) performance testing:
1. and (3) testing the adhesive force: the coating prepared in the embodiment 1-7 is used on a PCB, is irradiated by UV and the like within the range of 260-360 nm for curing, and the cured paint film is subjected to an adhesion test by referring to GB/T9286-1998, and the test results are recorded in the following table 1.
Table 1:
2. and (3) testing the impact resistance: test methods reference GB/T1454 and the test results are reported in Table 2 below.
Table 2:
Claims (7)
1. the photocureable coating is characterized by comprising the following preparation raw materials: polyester polyol, polyisocyanate, acrylate monomers, a catalyst, a reactive diluent, a photoinitiator and an auxiliary agent;
the acrylate monomer is hydroxyethyl methacrylate and methacrylate, and the weight ratio of the acrylate monomer to the methacrylate is 1: (0.3-0.7);
the reactive diluent is acrylate reactive diluent.
2. The photocurable coating of claim 1 wherein the polyisocyanate is selected from at least one of TMHDI, HDI, HTDI, MDI, IPDI, HMDI, TDI.
3. The light-cured coating according to claim 1, wherein the auxiliary agent comprises at least one of an accelerator, a color paste, a color developer, an antioxidant, an ultraviolet absorber, a filler and a coupling agent.
4. The photocurable coating according to claim 1, wherein the polyester polyol is an aliphatic polyester polyol and/or an aromatic polyester polyol.
5. The photocurable coating according to claim 1 or 4, wherein the polyester polyol is at least one selected from the group consisting of adipic acid-ethylene glycol-1, 4-butanediol polyester polyol, adipic acid-neopentyl glycol polyester polyol, adipic acid-1, 6-hexanediol polyester polyol, adipic acid-terephthalic acid-phthalic anhydride-diethylene glycol polyester polyol, and adipic acid-terephthalic anhydride-diethylene glycol polyester polyol.
6. The photocurable coating of claim 5 wherein the polyester polyol has an average molecular weight of 2000-.
7. A method for preparing the photo-curing coating according to any one of claims 1 to 6, comprising the steps of:
mixing the prepared raw materials, stirring, and obtaining the photocureable coating at the temperature of 30-70 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1421500A (en) * | 2001-11-29 | 2003-06-04 | 上海先鹏实业有限公司 | Coating material for reflecting film and its production process |
| CN108383974A (en) * | 2018-01-22 | 2018-08-10 | 武汉理工大学 | A kind of ultraviolet light solidification high-strength polyurethane acrylate and preparation method thereof |
| CN110066538A (en) * | 2019-04-10 | 2019-07-30 | 西安天元化工有限责任公司 | A kind of UV solidifies and commonly solidify the urethane composition of combination |
| CN110885664A (en) * | 2019-12-15 | 2020-03-17 | 今商科技(上海)有限公司 | Light-moisture curing adhesive with high-efficiency water-vapor barrier property and ultralow water absorption rate |
| CN113185909A (en) * | 2021-04-15 | 2021-07-30 | 佳化化学（抚顺）新材料有限公司 | Photocureable coating and preparation method and application thereof |
-
2021
- 2021-11-04 CN CN202111297279.0A patent/CN114621614B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1421500A (en) * | 2001-11-29 | 2003-06-04 | 上海先鹏实业有限公司 | Coating material for reflecting film and its production process |
| CN108383974A (en) * | 2018-01-22 | 2018-08-10 | 武汉理工大学 | A kind of ultraviolet light solidification high-strength polyurethane acrylate and preparation method thereof |
| CN110066538A (en) * | 2019-04-10 | 2019-07-30 | 西安天元化工有限责任公司 | A kind of UV solidifies and commonly solidify the urethane composition of combination |
| CN110885664A (en) * | 2019-12-15 | 2020-03-17 | 今商科技(上海)有限公司 | Light-moisture curing adhesive with high-efficiency water-vapor barrier property and ultralow water absorption rate |
| CN113185909A (en) * | 2021-04-15 | 2021-07-30 | 佳化化学（抚顺）新材料有限公司 | Photocureable coating and preparation method and application thereof |
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