CN110903431A - High-temperature-resistant multi-component epoxy resin leveling agent and preparation method thereof - Google Patents
High-temperature-resistant multi-component epoxy resin leveling agent and preparation method thereof Download PDFInfo
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- CN110903431A CN110903431A CN201911130077.XA CN201911130077A CN110903431A CN 110903431 A CN110903431 A CN 110903431A CN 201911130077 A CN201911130077 A CN 201911130077A CN 110903431 A CN110903431 A CN 110903431A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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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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- 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
- C09D7/47—Levelling agents
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses a high-temperature-resistant multi-component epoxy resin flatting agent and a preparation method thereof in the technical field related to epoxy resin; the high-temperature-resistant multi-component epoxy resin leveling agent comprises the following raw material components in parts by mole: 40-70 parts of butyl acrylate, 1-3 parts of hydroxypropyl acrylate, 1-3 parts of lauryl methacrylate, 1-3 parts of stearyl methacrylate, 11-16 parts of 2- (perfluorooctyl) ethyl methacrylate, 7-13 parts of methyl allyl alcohol, 8-23 parts of 10-hydroxy-2-decenoic acid, 1-3 parts of maleic anhydride, 1-4 parts of an initiator and 15-30 parts of an organic solvent; polar groups such as hydroxyl, carboxyl, anhydride and the like are introduced, so that the compatibility with the epoxy resin is improved, and the apparent leveling property and the glossiness are improved; the color of the product is not changed into yellow after high-temperature treatment; improves the corrosion resistance of the coating film and is suitable for various epoxy powder coatings.
Description
Technical Field
The invention relates to the technical field related to epoxy resin, and particularly relates to a high-temperature-resistant multi-component epoxy resin flatting agent and a preparation method thereof.
Background
The leveling agent is a common coating additive, can effectively reduce the surface tension of a finishing liquid, improve the leveling property and uniformity of the coating, improve the permeability of the coating and promote the coating to form a flat, smooth and uniform coating film in the drying film-forming process.
Factors influencing the leveling property of the coating are many, such as volatilization gradient and dissolution property of a solvent, surface tension of the coating, wet film thickness and surface tension gradient, rheological property of the coating, construction process and environment, and the like, wherein the most important factors are the surface tension of the coating, the surface tension gradient generated by a wet film in a film forming process and the surface tension homogenizing capability of a surface layer of the wet film. Improving the leveling of the coating requires consideration of adjusting the formulation and adding suitable auxiliaries to provide the coating with suitable surface tension and the ability to reduce surface tension gradients.
As long-chain resins having limited compatibility, polyacrylic acids, cellulose acetate butyrate and the like are generally used. These materials have low surface tension, and can reduce the surface tension between the coating material and the substrate to improve the wettability of the coating material to the substrate, remove gas molecules adsorbed on the surface of the coated solid, and prevent defects such as recesses, shrinkage cavities, orange peel and the like from being formed on the surface of the cured coating film due to the removal of the adsorbed gas molecules being too late.
However, the polybutyl acrylate belongs to a thermoplastic substance and does not contain a strong polar group in a molecule, so that the defects of easy film bleeding, poor wettability to a substrate, poor anti-cratering capability and the like are difficult to overcome, and the compactness and the surface effect of the formed film of the coating are influenced.
Disclosure of Invention
Aiming at the technical problems that the leveling agent in the prior art is easy to seep out of a coating film, has poor wettability to a base material and poor anti-cratering capability, and influences the compactness and the surface effect of a coating formed film, the invention provides a high-temperature-resistant multi-component epoxy resin leveling agent and a preparation method thereof.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a high-temperature-resistant multi-component epoxy resin flatting agent comprises the following raw material components in parts by mole: 40-70 parts of butyl acrylate, 1-3 parts of hydroxypropyl acrylate, 1-3 parts of lauryl methacrylate, 1-3 parts of stearyl methacrylate, 11-16 parts of 2- (perfluorooctyl) ethyl methacrylate, 7-13 parts of methyl allyl alcohol, 8-23 parts of 10-hydroxy-2-decenoic acid, 1-3 parts of maleic anhydride, 1-4 parts of initiator and 15-30 parts of organic solvent.
Preferably, the initiator is one or more of dibenzoyl peroxide, tert-butyl peroxybenzoate, azobisisobutyronitrile and azobisisovaleronitrile.
Preferably, the organic solvent is one of toluene, xylene, isopropanol, methyl ethyl ketone, propylene glycol methyl ether and butyl acetate.
The preparation method of the high-temperature-resistant multi-component epoxy resin leveling agent comprises the following steps:
s1) accurately weighing the butyl acrylate, adding the butyl acrylate into a reactor, and heating to a reflux state;
s2) accurately weighing the hydroxypropyl acrylate, the lauryl methacrylate, the stearyl methacrylate, the 2- (perfluorooctyl) ethyl methacrylate, the methyl allyl alcohol, the 10-hydroxy-2-decenoic acid, the maleic anhydride, the initiator and the organic solvent, and fully mixing to obtain a mixed solution;
s3) dropwise adding the mixed solution into the reflux liquid of the butyl acrylate at the temperature of 110-140 ℃, wherein the dropwise adding process is completed within 2-3 h;
s4) continuing to react for 3-6 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the product.
The operations of S1 and S2 may be performed simultaneously, or the operations of S2 may be completed before the operations of S1 are completed.
The invention has the following advantages:
1. the leveling agent of the invention has hydroxyl and carboxyl simultaneously, thus greatly improving the compatibility with epoxy resin, and greatly improving the apparent leveling property and the glossiness; and because the active group carboxyl participates in the curing reaction, the compactness of the coating is improved, thereby improving the corrosion resistance of the coating, and being suitable for various epoxy powder coatings;
2. polar groups such as acid anhydride and the like in the leveling agent can promote the compatibility with epoxy resin in the powder coating and the wettability of the coating and a substrate, and improve the leveling effect of the coating.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic diagram of a preparation process of the high temperature resistant multi-component epoxy resin leveling agent of the present invention.
Detailed Description
The following further describes embodiments of the present invention with reference to the drawings. It should be noted that the description of the embodiments is provided to help understanding of the present invention, but the present invention is not limited thereto. In addition, the technical features involved in the embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
All the raw materials used in the present invention, butyl acrylate, hydroxypropyl acrylate, lauryl methacrylate, stearyl methacrylate, 2- (perfluorooctyl) ethyl methacrylate, methacryl alcohol, 10-hydroxy-2-decenoic acid, maleic anhydride, dibenzoyl peroxide, tert-butyl peroxybenzoate, azobisisobutyronitrile, azobisisovaleronitrile, toluene, xylene, isopropanol, methyl ethyl ketone, propylene glycol methyl ether, and butyl acetate, are commonly sold in the market, and there is no need for special preparation.
Example 1
S1) accurately weighing 40 parts of butyl acrylate, adding the butyl acrylate into a reactor, heating to a reflux state and maintaining the reflux state;
s2) accurately weighing 1 part of hydroxypropyl acrylate, 1 part of lauryl methacrylate, 1 part of stearyl methacrylate, 11 parts of 2- (perfluorooctyl) ethyl methacrylate, 7 parts of methyl allyl alcohol, 8 parts of 10-hydroxy-2-decenoic acid, 1 part of maleic anhydride, 1 part of dibenzoyl peroxide as an initiator and 15 parts of toluene as an organic solvent, and fully mixing to obtain a mixed solution;
s3), dropwise adding the mixed solution into reflux of butyl acrylate at 110 ℃, wherein the dropwise adding process is completed within 2 h;
s4) continuing to react for 3 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the high-temperature-resistant multi-component epoxy resin leveling agent.
Example 2
S1) accurately weighing 50 parts of butyl acrylate, adding the butyl acrylate into a reactor, heating to a reflux state and maintaining the reflux state;
s2) accurately weighing 1.5 parts of hydroxypropyl acrylate, 1.5 parts of lauryl methacrylate, 1.5 parts of stearyl methacrylate, 12 parts of 2- (perfluorooctyl) ethyl methacrylate, 8 parts of methyl propenyl alcohol, 11 parts of 10-hydroxy-2-decenoic acid, 1.5 parts of maleic anhydride, 2 parts of azobisisobutyronitrile as an initiator and 18 parts of isopropanol as an organic solvent, and fully mixing to obtain a mixed solution;
s3), dropwise adding the mixed solution into reflux of butyl acrylate at 115 ℃, wherein the dropwise adding process is completed within 2.5 h;
s4) continuing to react for 4 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the high-temperature-resistant multi-component epoxy resin leveling agent.
Example 3
S1) accurately weighing 2 parts of hydroxypropyl acrylate, 2 parts of lauryl methacrylate, 2 parts of stearyl methacrylate, 13 parts of 2- (perfluorooctyl) ethyl methacrylate, 9 parts of methyl allyl alcohol, 14 parts of 10-hydroxy-2-decenoic acid, 2 parts of maleic anhydride, 2.5 parts of azobisisovaleronitrile as an initiator and 20 parts of methyl ethyl ketone as an organic solvent, and fully mixing to obtain a mixed solution;
s2) accurately weighing 60 parts of butyl acrylate, adding the butyl acrylate into a reactor, heating to a reflux state and maintaining the reflux state;
s3), dropwise adding the mixed solution into reflux of butyl acrylate at 120 ℃, wherein the dropwise adding process is completed within 2.5 h;
s4) continuing to react for 5 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the high-temperature-resistant multi-component epoxy resin leveling agent.
Example 4
S1) accurately weighing 2.5 parts of hydroxypropyl acrylate, 2.5 parts of lauryl methacrylate, 2.5 parts of stearyl methacrylate, 14 parts of 2- (perfluorooctyl) ethyl methacrylate, 10 parts of methyl allyl alcohol, 17 parts of 10-hydroxy-2-decenoic acid, 2.5 parts of maleic anhydride, 3 parts of azobisisovaleronitrile as an initiator and 25 parts of propylene glycol methyl ether as an organic solvent, and fully mixing to obtain a mixed solution;
s2) accurately weighing 65 parts of butyl acrylate, adding the butyl acrylate into a reactor, heating to a reflux state and maintaining the reflux state;
s3), dropwise adding the mixed solution into reflux of butyl acrylate at 125 ℃, wherein the dropwise adding process is completed within 2h and 45 min;
s4) continuing to react for 5.5 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the high-temperature-resistant multi-component epoxy resin leveling agent.
Example 5
S1) accurately weighing 3 parts of hydroxypropyl acrylate, 3 parts of lauryl methacrylate, 3 parts of stearyl methacrylate, 15 parts of 2- (perfluorooctyl) ethyl methacrylate, 11 parts of methyl allyl alcohol, 20 parts of 10-hydroxy-2-decenoic acid, 2.5 parts of maleic anhydride, 3 parts of tert-butyl peroxybenzoate as an initiator and 28 parts of butyl acetate as an organic solvent, and fully mixing to obtain a mixed solution;
s2) accurately weighing 68 parts of butyl acrylate, adding the butyl acrylate into a reactor, heating to a reflux state and maintaining the reflux state;
s3), dropwise adding the mixed solution into reflux of butyl acrylate at 130 ℃, wherein the dropwise adding process is completed within 3 h;
s4) continuing to react for 6 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the high-temperature-resistant multi-component epoxy resin leveling agent.
Example 6
S1) accurately weighing 70 parts of butyl acrylate, adding the butyl acrylate into a reactor, heating to a reflux state and maintaining the reflux state;
s2) accurately weighing 3 parts of hydroxypropyl acrylate, 3 parts of lauryl methacrylate, 3 parts of stearyl methacrylate, 16 parts of 2- (perfluorooctyl) ethyl methacrylate, 13 parts of methyl allyl alcohol, 23 parts of 10-hydroxy-2-decenoic acid, 3 parts of maleic anhydride, 4 parts of tert-butyl peroxybenzoate as an initiator and 30 parts of xylene as an organic solvent, and fully mixing to obtain a mixed solution;
s3), dropwise adding the mixed solution into reflux of butyl acrylate at 140 ℃, wherein the dropwise adding process is completed within 3 h;
s4) continuing to react for 6 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the high-temperature-resistant multi-component epoxy resin leveling agent.
Example 7
S1) accurately weighing 40 parts of butyl acrylate, adding the butyl acrylate into a reactor, heating to a reflux state and maintaining the reflux state;
meanwhile, 2 parts of hydroxypropyl acrylate, 2 parts of lauryl methacrylate, 2 parts of stearyl methacrylate, 13 parts of 2- (perfluorooctyl) ethyl methacrylate, 9 parts of methyl allyl alcohol, 14 parts of 10-hydroxy-2-decenoic acid, 2 parts of maleic anhydride, 2.5 parts of azobisisovaleronitrile as an initiator and 20 parts of methyl ethyl ketone as an organic solvent are accurately weighed and fully mixed to obtain a mixed solution;
s2, dropwise adding the mixed solution into reflux of butyl acrylate at 120 ℃, wherein the dropwise adding process is completed within 2.5 h;
s3) continuing to react for 5 h;
s4) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the high-temperature-resistant multi-component epoxy resin leveling agent.
In the present invention, the raw material components that perform the same function may be replaced with each other in different embodiments, for example, in the case of an initiator, wherein the dibenzoyl peroxide used in embodiment 1 may be replaced with all or part of tert-butyl peroxybenzoate, azobisisobutyronitrile, and azobisisovaleronitrile in other embodiments, for example, 2 parts of azobisisobutyronitrile in embodiment 2 may be replaced with all 2 parts of dibenzoyl peroxide, or partially replaced with a mixture of 1 part of dibenzoyl peroxide and 1 part of dibenzoyl peroxide; other alternatives are the same and will not be described again.
Comparative example 1
In this comparative example, the raw materials, reaction conditions and preparation process used were the same as in example 1 except that butyl acrylate was not used.
Comparative example 2
In this comparative example, the raw materials, reaction conditions and preparation process used were the same as in example 2 except that 2- (perfluorooctyl) ethyl methacrylate was not used.
Comparative example 3
In this comparative example, the starting materials, reaction conditions and preparation process used were the same as in example 3, except that 10-hydroxy-2-decenoic acid was not used.
The finished products obtained in the examples of the invention and the finished products obtained in the comparative examples were mixed in the same powder coating under the same conditions, sprayed on the same substrate, and cured at 180 ℃/15min to obtain a coating layer.
The detection of the coating index is carried out according to GB/T21776-2008 'Standard guide for powder coating and coating thereof' and GB/T9274-1988A method (soaking method), and the performance detection data are as follows:
through comparison, the leveling agent prepared by the technical scheme of the invention has hydroxyl and carboxyl simultaneously, so that the compatibility with epoxy resin is greatly improved, the apparent leveling property and the glossiness are greatly improved compared with the proportion, and the compactness of a coating is improved due to the participation of active group carboxyl in a curing reaction, so that the corrosion resistance of the coating is improved, and the leveling agent is suitable for various epoxy powder coatings; the paint does not turn yellow after high-temperature treatment, thereby greatly improving the surface defect of a powder coating film and improving the leveling effect; polar groups such as acid anhydride and the like can promote the compatibility with epoxy resin in the powder coating and the wettability of the coating and a substrate, and improve the leveling effect of the coating.
The embodiments of the present invention have been described in detail with reference to the accompanying drawings, but the present invention is not limited to the described embodiments. It will be apparent to those skilled in the art that various changes, modifications, substitutions and alterations can be made in the embodiments without departing from the principles and spirit of the invention, and these embodiments are within the scope of the invention.
Claims (5)
1. A high-temperature-resistant multi-component epoxy resin leveling agent is characterized in that: comprises the following raw material components in parts by mole: 40-70 parts of butyl acrylate, 1-3 parts of hydroxypropyl acrylate, 1-3 parts of lauryl methacrylate, 1-3 parts of stearyl methacrylate, 11-16 parts of 2- (perfluorooctyl) ethyl methacrylate, 7-13 parts of methyl allyl alcohol, 8-23 parts of 10-hydroxy-2-decenoic acid, 1-3 parts of maleic anhydride, 1-4 parts of initiator and 15-30 parts of organic solvent.
2. The high temperature resistant multi-component epoxy resin leveling agent according to claim 1, wherein: the initiator is one or more of dibenzoyl peroxide, tert-butyl peroxybenzoate, azobisisobutyronitrile and azobisisovaleronitrile.
3. A high temperature resistant multi-component epoxy resin leveling agent according to claim 1 or 2, characterized in that: the organic solvent is one of toluene, xylene, isopropanol, methyl ethyl ketone, propylene glycol methyl ether and butyl acetate.
4. A preparation method of the high-temperature-resistant multi-component epoxy resin leveling agent according to any one of claims 1 to 3, characterized by comprising the following steps: the method comprises the following steps:
s1) accurately weighing the butyl acrylate, adding the butyl acrylate into a reactor, and heating to a reflux state;
s2) accurately weighing the hydroxypropyl acrylate, the lauryl methacrylate, the stearyl methacrylate, the 2- (perfluorooctyl) ethyl methacrylate, the methyl allyl alcohol, the 10-hydroxy-2-decenoic acid, the maleic anhydride, the initiator and the organic solvent, and fully mixing to obtain a mixed solution;
s3) dropwise adding the mixed solution into the reflux liquid of the butyl acrylate at the temperature of 110-140 ℃, wherein the dropwise adding process is completed within 2-3 h;
s4) continuing to react for 3-6 h;
s5) carrying out reduced pressure distillation until no distillate exists, and cooling the obtained distillate to obtain the product.
5. The preparation method of the high temperature resistant multi-component epoxy resin leveling agent according to claim 4, wherein: s1 is performed simultaneously with the operation of S2 or after completing the operation of S2 and then completing the operation of S1.
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| CN112094529A (en) * | 2020-09-27 | 2020-12-18 | 湖北淡雅香生物科技股份有限公司 | Processing method of flexo-printing environment-friendly tipping paper water-based ink |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112094529A (en) * | 2020-09-27 | 2020-12-18 | 湖北淡雅香生物科技股份有限公司 | Processing method of flexo-printing environment-friendly tipping paper water-based ink |
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Application publication date: 20200324 |