CN111285957A - Water dispersible hydroxy acrylic resin and preparation method thereof - Google Patents
Water dispersible hydroxy acrylic resin and preparation method thereof Download PDFInfo
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- 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
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- 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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- 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
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C08F4/00—Polymerisation catalysts
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- C08F4/00—Polymerisation catalysts
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/068—Copolymers with monomers not covered by C09D133/06 containing glycidyl groups
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Abstract
The invention relates to a water dispersible hydroxy acrylic resin which is prepared from the following raw materials in parts by mass: 8-12 parts of methyl methacrylate, 5-8 parts of isooctyl acrylate, 3-6 parts of lauryl methacrylate, 3-8 parts of hydroxyethyl methacrylate, 3-5 parts of hydroxypropyl methacrylate, 6-10 parts of acrylic acid, 1-4 parts of glycidyl versatate, 2-5 parts of glycidyl methacrylate, 1-2 parts of an initiator, 0.5-1 part of a chain transfer agent, 5-10 parts of an environment-friendly cosolvent, 2-3 parts of an amine neutralizer and 40-45 parts of deionized water. The invention also relates to a preparation method of the water dispersible hydroxyacrylic acid resin. The product of the invention has excellent fullness, luster, hardness and weather resistance, and does not change color or turn yellow after being exposed outdoors for one year.
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to a water dispersible hydroxy acrylic resin and a preparation method thereof.
Background
The acrylic resin is a coating matrix resin with high strength and high gloss, and has high application value in the fields of vehicle coating, mechanical protection and the like. At present, domestic high-hardness industrial coatings are mainly solvent-based bi-component coatings, and the coatings have high organic solvent content, so that the coatings cause great environmental pollution and great harm to the health of constructors and users. In addition, as organic solvents such as toluene, xylene and the like belong to flammable and explosive dangerous articles, the organic solvents bring great danger to the storage and transportation of products, and have important practical significance for producing high-performance water-based resin along with the improvement of domestic environmental protection requirements.
Disclosure of Invention
The invention aims to provide a water-dispersible hydroxyacrylic resin and a preparation method thereof, and aims to solve the problems of high VOC content, pungent smell and poor comprehensive performance of the resin in the existing product.
The technical scheme of the invention is as follows:
the water dispersible hydroxy acrylic resin is prepared from the following raw materials in parts by mass:
8-12 parts of methyl methacrylate, 5-8 parts of isooctyl acrylate, 3-6 parts of lauryl methacrylate, 3-8 parts of hydroxyethyl methacrylate, 3-5 parts of hydroxypropyl methacrylate, 6-10 parts of acrylic acid, 1-4 parts of glycidyl versatate, 2-5 parts of glycidyl methacrylate, 1-2 parts of an initiator, 0.5-1 part of a chain transfer agent, 5-10 parts of an environment-friendly cosolvent, 2-3 parts of an amine neutralizer and 40-45 parts of deionized water.
Preferably, the initiator comprises azobisisobutyronitrile, benzoyl peroxide and tert-butyl peroxybenzoate, and the mass ratio of the azobisisobutyronitrile to the benzoyl peroxide to the tert-butyl peroxybenzoate is 2:1: 1.
Preferably, the chain transfer agent is 2, 4-diphenyl-4-methyl-1-pentene.
Preferably, the environment-friendly cosolvent is an environment-friendly cosolvent X-K1 produced by Gansu Baolio.
Preferably, the amine neutralizer is a GC-2795 alcohol amine ether organic matter.
A preparation method of water dispersible hydroxyacrylic resin comprises the following steps:
step A, preparation of a reaction substrate: uniformly mixing the environment-friendly cosolvent, the tertiary carbonic acid glycidyl ester, the glycidyl methacrylate and one fifth of the 2, 4-diphenyl-4-methyl-1-pentene, heating to the temperature of 100 ℃ and 130 ℃, and stirring for 30-45min for later use;
step B, preparing monomer mixed liquor: uniformly mixing and dissolving methyl methacrylate, isooctyl acrylate, lauryl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, four fifths of 2, 4-diphenyl-4-methyl-1-pentene and an initiator under stirring;
step C, preparing acrylic resin: heating the reaction substrate to 80-100 ℃, dropwise adding the monomer mixed solution obtained in the step B into the reaction substrate within 3-4h, preserving the heat for 3-3.5h after the dropwise adding is finished, and cooling to 60-80 ℃;
step D extraction solvent: distilling at 60-80 deg.C under reduced pressure of 0.03MPa until no organic matter is distilled off, and separating out organic solvent in the dispersion;
step E neutralization and dispersion: adding an amine neutralizer into the acrylic resin after the organic solvent is separated in the step D, controlling the neutralization degree to be between 100 and 110 percent, and stirring for 20 to 30 min; adding deionized water, and dispersing for 30-35min under the high-speed stirring of 2000-2500r/min to obtain the water-dispersible hydroxyacrylic resin.
The invention has the following characteristics:
1. the preparation method of the low-VOC water-dispersible hydroxy acrylic resin uses an environment-friendly cosolvent, greatly reduces the VOC of the resin on the premise of not influencing the dilution capacity, has the content of less than 50g/L, is lower compared with similar resin products, can be used for co-grinding, and is an energy-saving and environment-friendly high-performance product.
2. The 2, 4-diphenyl-4-methyl-1-pentene chain transfer agent in the water-dispersible hydroxyacrylic resin has a special function, can uniformly polymerize hydroxyacrylic acid to form a more compact paint film, can improve the bond energy of the hydroxyacrylic resin, is not easy to break, and improves the ultraviolet irradiation resistance of the hydroxyacrylic resin.
3. Azodiisobutyronitrile, benzoyl peroxide and tert-butyl peroxybenzoate are added according to the proportion of 2:1:1, and the activation energy required by resin synthesis can be reduced on the premise of not influencing the resin performance, so that the energy consumption is saved, and the energy-saving and environment-friendly effects are achieved.
4. The water dispersible hydroxyl acrylic resin product of the invention uses GC-2795 alcohol amine ether organic matter as neutralizing agent, can meet the performance requirements of the existing product, the prepared resin has no pungent smell, reduces the pollution to constructors and environment, and all performances are also improved; meets the requirements of various national mandatory standards and technologies, and breaks the problem that domestic high-performance resin depends on import; the cost is also lower, and the method is beneficial to industrial production, popularization and use of products.
Compared with the prior art, the invention has the following beneficial effects:
1. the water-dispersible hydroxyl acrylic resin disclosed by the invention has the excellent characteristics of a solvent type hydroxyl acrylic resin, the compactness of a paint film is increased, the permeability is reduced, the shielding effect of the paint film is improved, the comprehensive performance has obvious advantages, the prepared finish paint is water-resistant for more than 3 months, and has excellent fullness, gloss, hardness and weather resistance, and the finish paint does not change color or turn yellow after being exposed to the sun for one year outdoors.
2. The water dispersible hydroxy acrylic resin disclosed by the invention is uniformly polymerized into an ideal structure through the unique actions of chain initiation and chain transfer, the hardness, medium resistance, gloss and anti-fouling capability of a paint film are obviously improved, the freeze-thaw stability and the heat storage property are excellent, no abnormality exists after 5 times of freeze-thaw cycle, no abnormality exists after 30 days of heat storage, and the water dispersible hydroxy acrylic resin can be stored at any temperature.
3. The water dispersible hydroxy acrylic resin reduces VOC content, greatly reduces VOC emission in production and construction processes, is safe and environment-friendly, can be widely used for coating in steel structures, automobiles and other aspects, has no disadvantage of unstable storage of emulsion products and no pungent ammonia odor, and is one of the most ideal high-performance water-based resin products.
4. The preparation method of the water dispersible hydroxyl acrylic resin adopts a chemical method, uses the environment-friendly cosolvent, has the dilution capability far higher than that of other cosolvents, has very small addition amount and little influence on human bodies, and is one of the expected cosolvents in aqueous products.
Detailed Description
The following examples further illustrate the invention but are not intended to limit the invention in any way.
Methyl methacrylate, isooctyl acrylate, lauryl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, glycidyl versatate and glycidyl methacrylate used in the examples are qualified products of any manufacturers.
The initiators of azodiisobutyronitrile, benzoyl peroxide and tert-butyl peroxybenzoate are respectively produced by one-tillage chemical industry in Changzhou city, auxiliary agent factories in Lanzhou city and Pectine chemical industry in Jiangsu province; the chain transfer agent 2, 4-diphenyl-4-methyl-1-pentene is YX-301 produced by North-West Yongxin coating company Limited; the environment-friendly cosolvent is X-K1 produced by Gansu Baoling; the amine neutralizer is GC-2795 alcohol amine ether organic matters produced by Guangzhou Zhonghua trade company Limited.
The amounts of the starting materials for the water-dispersible hydroxyacrylic resins of examples 1 to 3 are given in Table 1 in g.
TABLE 1 dosage of Water-dispersible hydroxyacrylic resin raw materials
The raw material dosage is shown in table 1, and the specific preparation process is as follows:
example 1
Step A, preparation of a reaction substrate: uniformly mixing the environment-friendly cosolvent, the glycidyl versatate, the glycidyl methacrylate and one fifth of 2, 4-diphenyl-4-methyl-1-pentene by mass, heating to 130 ℃, and stirring for 30min for later use.
Step B, preparing monomer mixed liquor: methyl methacrylate, isooctyl acrylate, lauryl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, four fifths of 2, 4-diphenyl-4-methyl-1-pentene, azobisisobutyronitrile, benzoyl peroxide and tert-butyl peroxybenzoate are mixed and dissolved uniformly under stirring.
Step C, preparing acrylic resin: and (4) heating the reaction substrate to 80 ℃, dropwise adding the monomer mixed solution obtained in the step (B) within 4h, preserving the temperature for 3.5h after dropwise adding is finished, and then cooling to 60 ℃.
Step D extraction solvent: the organic solvent in the dispersion was separated by distillation at 60 ℃ under reduced pressure of 0.03 MPa.
Step E neutralization and dispersion: adding GC-2795 alcohol amine ether organic matters into the acrylic resin prepared in the step D, controlling the neutralization degree to be 100%, and stirring for 20 min; adding deionized water, and dispersing for 35min under high-speed stirring of 2000r/min to obtain the water dispersible hydroxy acrylic resin.
Example 2
Step A, preparation of a reaction substrate: uniformly mixing the environment-friendly cosolvent, the glycidyl versatate, the glycidyl methacrylate and one fifth of 2, 4-diphenyl-4-methyl-1-pentene by mass, heating to 100 ℃, and stirring for 45min for later use.
Step B, preparing monomer mixed liquor: methyl methacrylate, isooctyl acrylate, lauryl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, four fifths of 2, 4-diphenyl-4-methyl-1-pentene, azobisisobutyronitrile, benzoyl peroxide and tert-butyl peroxybenzoate are mixed and dissolved uniformly under stirring.
Step C, preparing acrylic resin: and (4) heating the reaction substrate to 100 ℃, dropwise adding the monomer mixed solution obtained in the step (B) within 3h, preserving the temperature for 3.3h after dropwise adding is finished, and then cooling to 70 ℃.
Step D extraction solvent: the organic solvent in the dispersion was separated by distillation at 70 ℃ under reduced pressure of 0.03 MPa.
Step E neutralization and dispersion: adding GC-2795 alcohol amine ether organic matters into the acrylic resin prepared in the step D, controlling the neutralization degree to be 105%, and stirring for 25 min; adding deionized water, and dispersing for 33min under high-speed stirring of 2200r/min to obtain the water dispersible hydroxyacrylic resin.
Example 3
Step A, preparation of a reaction substrate: uniformly mixing the environment-friendly cosolvent, the glycidyl versatate, the glycidyl methacrylate and one fifth of 2, 4-diphenyl-4-methyl-1-pentene by mass, heating to 120 ℃, and stirring for 35min for later use.
Step B, preparing monomer mixed liquor: methyl methacrylate, isooctyl acrylate, lauryl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, four fifths of 2, 4-diphenyl-4-methyl-1-pentene, azobisisobutyronitrile, benzoyl peroxide and tert-butyl peroxybenzoate are mixed and dissolved uniformly under stirring.
Step C, preparing acrylic resin: and (3) heating the reaction substrate to 90 ℃, dropwise adding the monomer mixed solution obtained in the step (B) within 3.5h, preserving the heat for 3h after the dropwise adding is finished, and then cooling to 80 ℃.
Step D extraction solvent: the organic solvent in the dispersion was separated by distillation at 80 ℃ under reduced pressure of 0.03 MPa.
Step E neutralization and dispersion: adding GC-2795 alcohol amine ether organic matters into the acrylic resin prepared in the step D, controlling the neutralization degree to be 110%, and stirring for 30 min; adding deionized water, and dispersing for 30min under the high-speed stirring of 2500r/min to obtain the water-dispersible hydroxyacrylic resin.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications can be made without departing from the technical principle of the present invention, and these modifications should also be considered as the protection scope of the present invention.
The result of the detection
The results of the performance tests of the coatings prepared using the water-dispersible hydroxyacrylic resins are shown in table 2:
TABLE 2 Water-dispersible hydroxyacrylic resin coating test results
Claims (6)
1. A water-dispersible hydroxyacrylic resin characterized by: the feed is prepared from the following raw materials in parts by mass:
8-12 parts of methyl methacrylate, 5-8 parts of isooctyl acrylate, 3-6 parts of lauryl methacrylate, 3-8 parts of hydroxyethyl methacrylate, 3-5 parts of hydroxypropyl methacrylate, 6-10 parts of acrylic acid, 1-4 parts of glycidyl versatate, 2-5 parts of glycidyl methacrylate, 1-2 parts of an initiator, 0.5-1 part of a chain transfer agent, 5-10 parts of an environment-friendly cosolvent, 2-3 parts of an amine neutralizer and 40-45 parts of deionized water.
2. The water-dispersible hydroxyacrylic resin according to claim 1, wherein: the initiator comprises azobisisobutyronitrile, benzoyl peroxide and tert-butyl peroxybenzoate, and the mass ratio of the azobisisobutyronitrile to the benzoyl peroxide to the tert-butyl peroxybenzoate is 2:1: 1.
3. The water-dispersible hydroxyacrylic resin according to claim 1, wherein: the chain transfer agent is 2, 4-diphenyl-4-methyl-1-pentene.
4. The water-dispersible hydroxyacrylic resin according to claim 1, wherein: the environment-friendly cosolvent is an environment-friendly cosolvent X-K1 produced by Gansu Baoling.
5. The water-dispersible hydroxyacrylic resin according to claim 1, wherein: the amine neutralizer is a GC-2795 alcohol amine ether organic matter.
6. A process for preparing a water-dispersible hydroxyacrylic resin according to any one of claims 1 to 5, characterized in that: the method comprises the following steps:
step A, preparation of a reaction substrate: uniformly mixing the environment-friendly cosolvent, the tertiary carbonic acid glycidyl ester, the glycidyl methacrylate and one fifth of 2, 4-diphenyl-4-methyl-1-pentene by mass, heating to the temperature of 100 ℃ and 130 ℃, and stirring for 30-45min for later use;
step B, preparing monomer mixed liquor: uniformly mixing and dissolving methyl methacrylate, isooctyl acrylate, lauryl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, four fifths of 2, 4-diphenyl-4-methyl-1-pentene and an initiator by mass under stirring;
step C, preparing acrylic resin: heating the reaction substrate to 80-100 ℃, dropwise adding the monomer mixed solution obtained in the step B into the reaction substrate within 3-4h, preserving the heat for 3-3.5h after the dropwise adding is finished, and cooling to 60-80 ℃;
step D extraction solvent: distilling at 60-80 deg.C under reduced pressure of 0.03MPa until no organic matter is distilled off, and separating out organic solvent in the dispersion;
step E neutralization and dispersion: adding an amine neutralizer into the acrylic resin after the organic solvent is separated in the step D, controlling the neutralization degree to be between 100 and 110 percent, and stirring for 20 to 30 min; adding deionized water, and dispersing for 30-35min under the high-speed stirring of 2000-2500r/min to obtain the water-dispersible hydroxyacrylic resin.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112142904A (en) * | 2020-10-14 | 2020-12-29 | 西北永新涂料有限公司 | Water-based high-hardness water-resistant acrylic resin and preparation method thereof |
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| CN112142904A (en) * | 2020-10-14 | 2020-12-29 | 西北永新涂料有限公司 | Water-based high-hardness water-resistant acrylic resin and preparation method thereof |
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