CN108409904B - Hydroxyl acrylic acid dispersoid modified by glycidyl p-hydroxybenzoate and preparation method thereof - Google Patents
Hydroxyl acrylic acid dispersoid modified by glycidyl p-hydroxybenzoate 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
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- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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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
- C08F220/16—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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- 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
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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
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- 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
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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Abstract
The invention relates to a hydroxyl acrylic acid dispersoid modified by p-hydroxybenzoic acid glycidyl ester and a preparation method thereof, wherein the novel hydroxyl acrylic acid dispersoid modified by the p-hydroxybenzoic acid glycidyl ester is prepared by a one-pot method by selecting a peracid compound which can provide active hydrogen and can also be used as an initiator; the use of reaction reagents, cosolvents and the like is reduced in the preparation process, and the prepared hydroxyl acrylic acid dispersoid has excellent performance, high solid content and hydroxyl value and low VOC content; the hydroxyl acrylic acid dispersoid prepared by the invention has excellent water resistance and ethanol resistance.
Description
Technical Field
The invention belongs to the field of materials, and particularly relates to a hydroxyl acrylic acid dispersoid modified by p-hydroxybenzoic acid glycidyl ester and a preparation method thereof.
Background
The water-based bi-component polyurethane is mainly prepared by curing and crosslinking a hydroxyl functional group in a water-based hydroxyl acrylic acid dispersoid and a hydroxyl reactant water-based polyisocyanate curing agent. Most of hydroxyl acrylic acid dispersions on the market are monohydroxy groups, and the hydroxyl groups are mainly introduced by acrylate monomers with hydroxyl groups, but in some special industrial fields, higher hydroxyl group content is often needed, if the hydroxyl groups are introduced only by the monohydroxy acrylate monomers, the cost is increased greatly, and the introduction of the hydroxyl groups by special low-cost monomer grafting becomes an important means for solving the problem. The introduction of the epoxy group can obtain hydroxyl, so that the content of the hydroxyl in the system is increased, and the adhesive force of the resin to a substrate is greatly improved.
The glycidyl paraben can be introduced into the resin by reacting the active epoxy groups with a compound containing active hydrogen carboxyl groups. The invention selects peracid compounds which can provide active hydrogen and can also be used as an initiator, and prepares a novel hydroxyl acrylic acid dispersoid modified by p-hydroxybenzoic acid glycidyl ester by a one-pot method. The invention not only has simple synthesis process, but also the prepared hydroxyl acrylic acid dispersoid has excellent performance, the solid content is 53.5-54.5 +/-2.0 percent, the viscosity is 1830-1856mpa.s, the hydroxyl value is 5.8 +/-0.2, and the VOC content is 30-33 mu g/g.
Disclosure of Invention
The invention provides a glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersion, which is characterized in that the preparation method of the glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersion comprises the following steps:
according to the weight parts, 5-8 parts of glycidyl p-hydroxybenzoate, 1.5-2.5 parts of peracid, 2-3 parts of cosolvent and 30-40 parts of acrylate monomer are uniformly mixed, heated to 50-60 ℃ for reaction for 0.5-1.0h, heated to 120-135 ℃ for continuous reaction for 1-2h, cooled to 70-80 ℃, added with a neutralizing agent, added with deionized water, stirred and dispersed for 1-2h, and discharged, so that the glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersoid is obtained.
The peracid is preferably peroxybenzoic acid or m-chloroperoxybenzoic acid; the cosolvent is preferably ethylene glycol butyl ether, propylene glycol butyl ether and propylene glycol methyl ether; the acrylic ester monomer is selected from one or a mixture of methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate and hydroxyethyl methacrylate; the neutralizing agent is one or a mixture of triethylamine, N-dimethylethanolamine, ammonia water or tripropylamine.
Another embodiment of the present invention provides a method for preparing the above-mentioned glycidyl paraben-modified hydroxyacrylic acid dispersion, which is characterized by comprising the steps of:
according to the weight parts, 5-8 parts of glycidyl p-hydroxybenzoate, 1.5-2.5 parts of peracid, 2-3 parts of cosolvent and 30-40 parts of acrylate monomer are uniformly mixed, heated to 50-60 ℃ for reaction for 0.5-1.0h, heated to 120-135 ℃ for continuous reaction for 1-2h, cooled to 70-80 ℃, added with a neutralizing agent, added with deionized water, stirred and dispersed for 1-2h, and discharged, so that the glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersoid is obtained.
The peracid is preferably peroxybenzoic acid or m-chloroperoxybenzoic acid; the cosolvent is preferably ethylene glycol butyl ether, propylene glycol butyl ether and propylene glycol methyl ether; the acrylic ester monomer is selected from one or a mixture of methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate and hydroxyethyl methacrylate; the neutralizing agent is one or a mixture of triethylamine, N-dimethylethanolamine, ammonia water or tripropylamine.
The solid content of the hydroxyl acrylic acid dispersoid modified by the glycidyl p-hydroxybenzoate prepared by the preparation method is 53.5-54.5 +/-2.0 percent, the viscosity is 1830-1856mpa.s, the hydroxyl value is 5.8 +/-0.2, and the VOC content is 30-33 mu g/g.
Another embodiment of the present invention provides the use of the above-described glycidyl paraben modified hydroxyacrylic acid dispersion for the preparation of paints and coatings.
Compared with the prior art, the invention has the advantages that: (1) according to the invention, a peracid compound can provide active hydrogen and can also be used as an initiator, and a novel hydroxyl acrylic acid dispersoid modified by p-hydroxybenzoic acid glycidyl ester is prepared by a one-pot method; (2) the synthetic process of the invention reduces the use of reaction reagents, cosolvents and the like, and the prepared hydroxyl acrylic acid dispersoid has excellent performance, high solid content and hydroxyl value and low VOC content; and (3) the hydroxyl acrylic dispersion prepared by the invention has excellent water resistance and ethanol resistance.
Drawings
FIG. 1 is a particle size distribution diagram of product A.
Detailed Description
In order to facilitate a further understanding of the invention, the following examples are provided to illustrate it in more detail. However, these examples are only for better understanding of the present invention and are not intended to limit the scope or the principle of the present invention, and the embodiments of the present invention are not limited to the following.
Example 1
5g of glycidyl p-hydroxybenzoate, 1.5g of m-chloroperoxybenzoic acid, 2.0g of ethylene glycol butyl ether, 10g of methyl methacrylate, 10g of butyl acrylate and 10g of hydroxyethyl methacrylate are mixed uniformly, heated to 50 ℃ for reaction for 1.0h, heated to 135 ℃ for continuous reaction for 1h, cooled to 80 ℃, added with a proper amount of N, N-dimethylethanolamine for neutralization, added with a proper amount of deionized water for stirring and dispersion for 1-2h, and discharged, thus obtaining the glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersoid (hereinafter referred to as product A).
Example 2
Uniformly mixing 8g of glycidyl p-hydroxybenzoate, 2.5g of m-chloroperoxybenzoic acid, 3.0g of propylene glycol butyl ether, 18g of methyl methacrylate and 22g of methyl acrylate, heating to 60 ℃, reacting for 0.5h, heating to 120 ℃, continuing to react for 2h, cooling to 70 ℃, adding an appropriate amount of triethylamine for neutralization, adding an appropriate amount of deionized water, stirring and dispersing for 1-2h, and discharging to obtain the glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersoid (hereinafter referred to as a product B).
Example 3
5g of glycidyl p-hydroxybenzoate, 1.5g of m-chloroperoxybenzoic acid, 2.0g of ethylene glycol butyl ether, 10g of methyl methacrylate, 10g of butyl acrylate and 10g of hydroxyethyl methacrylate are mixed uniformly, the mixture is directly heated to 135 ℃ to continue to react for 1 hour, then the temperature is reduced to 80 ℃, a proper amount of N, N-dimethylethanolamine is added for neutralization, a proper amount of deionized water is added for stirring and dispersing for 1-2 hours, and then the product C is obtained after discharging.
Example 4
5g of tertiary carbonic acid glycidyl ester (E10P), 1.5g of m-chloroperoxybenzoic acid, 2.0g of ethylene glycol butyl ether, 10g of methyl methacrylate, 10g of butyl acrylate and 10g of hydroxyethyl methacrylate are mixed uniformly, heated to 50 ℃ for reaction for 1.0h, heated to 135 ℃ for continuous reaction for 1h, cooled to 80 ℃, added with proper amount of N, N-dimethylethanolamine for neutralization, added with proper amount of deionized water, stirred and dispersed for 1-2h, and discharged, thus obtaining the product D.
Example 5
5g of glycidyl p-hydroxybenzoate, 0.5g of m-chloroperoxybenzoic acid, 2.0g of butyl glycol ether, 10g of methyl methacrylate, 10g of butyl acrylate and 10g of hydroxyethyl methacrylate are mixed uniformly, heated to 50 ℃ for reaction for 1.0h, heated to 135 ℃ for continuous reaction for 1h, cooled to 80 ℃, added with a proper amount of N, N-dimethylethanolamine for neutralization, added with a proper amount of deionized water, stirred and dispersed for 1-2h, and then discharged, thus obtaining the product E.
The particle size range of product A, B, 100-300nm, is limited to the space where only the particle size distribution of product A is shown.
Example 6
The viscosity of the dispersions of the examples was measured using a rotational viscometer and the solids content of the dispersions was measured using a 160 ℃ bake for 1 h. The specific data are shown in Table 1.
TABLE 1
"-" indicates not measured.
Example 7
The hydroxyl acrylic acid dispersoid of the product A, the product of the market model 1121 and the product of the Chinese invention patent (application number: 201611200208.3) in the example 1 (the patent product for short) and the polyisocyanate curing agent are crosslinked to prepare paint, and the specific data are shown in the table 2 in a comparison experiment.
TABLE 2
As can be seen from the test results of examples 6-7, the glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersion prepared by the method disclosed by the invention is high in solid content and hydroxyl value, low in VOC (volatile organic compound) content, excellent in water resistance and ethanol resistance in paint preparation, free from foaming, falling and discoloration after 2 days, and more than or equal to 100 times of ethanol wiping resistance.
Claims (5)
1. A glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersion, characterized in that the preparation method of the glycidyl p-hydroxybenzoate modified hydroxyacrylic acid dispersion comprises the following steps:
according to the weight portion, 5-8 portions of parahydroxybenzoic acid glycidyl ester, 1.5-2.5 portions of peracid, 2-3 portions of cosolvent and 30-40 portions of acrylate monomer are mixed evenly and heated to 50-60 portionsoC, after the reaction for 0.5 to 1.0 hour, the temperature is raised to 120-phase 135oC, continuously reacting for 1-2h, cooling to 70-80 ℃, adding a neutralizing agent, adding deionized water, stirring and dispersing for 1-2h, and discharging to obtain the p-hydroxybenzoic acid glycidyl ester modified hydroxy acrylic acid dispersoid; the peracid is selected from peroxybenzoic acid and m-chloroperoxybenzoic acid; the cosolvent is selected from ethylene glycol butyl ether, propylene glycol butyl ether and propylene glycol methyl ether.
2. The glycidyl p-hydroxybenzoate modified acrylic dispersion as claimed in claim 1, wherein the acrylic ester monomer is selected from one or more of methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate and hydroxyethyl methacrylate.
3. The glycidyl p-hydroxybenzoate modified acrylic dispersion as claimed in claim 1, wherein the neutralizing agent is selected from one or more of triethylamine, N-dimethylethanolamine, ammonia water or tripropylamine.
4. The glycidyl paraben-modified hydroxyacrylic acid dispersion of any of claims 1-3, wherein the dispersion has a solid content of 53.5. + -. 0.2 to 54.5. + -. 0.2%, a viscosity of 1830 and 1856mpa.s, a hydroxyl number of 5.8. + -. 0.2 and a VOC content of 30 to 33. mu.g/g.
5. Use of the glycidyl paraben modified hydroxyacrylic acid dispersion of any of claims 1 to 4 for the preparation of paints and coatings.
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| CN201810285788.3A CN108409904B (en) | 2018-04-02 | 2018-04-02 | Hydroxyl acrylic acid dispersoid modified by glycidyl p-hydroxybenzoate and preparation method thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101457005A (en) * | 2008-12-25 | 2009-06-17 | 浙江环达漆业集团有限公司 | Method for preparing hydroxyl acrylic acid water dispersoid |
| CN102850703A (en) * | 2011-06-27 | 2013-01-02 | 上海涂料有限公司技术中心 | Method for preparing hydroxy-containing polyacrylate secondary aqueous dispersion |
| CN103265881A (en) * | 2013-05-30 | 2013-08-28 | 苏州艾特斯环保材料有限公司 | High temperature resistant anticorrosive paint comprising polyaryl organic silicon resin |
| CN106117419A (en) * | 2016-07-26 | 2016-11-16 | 立邦涂料（中国）有限公司 | A kind of acrylic acid water dispersoid of hydroxyl and preparation method thereof |
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- 2018-04-02 CN CN201810285788.3A patent/CN108409904B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101457005A (en) * | 2008-12-25 | 2009-06-17 | 浙江环达漆业集团有限公司 | Method for preparing hydroxyl acrylic acid water dispersoid |
| CN102850703A (en) * | 2011-06-27 | 2013-01-02 | 上海涂料有限公司技术中心 | Method for preparing hydroxy-containing polyacrylate secondary aqueous dispersion |
| CN103265881A (en) * | 2013-05-30 | 2013-08-28 | 苏州艾特斯环保材料有限公司 | High temperature resistant anticorrosive paint comprising polyaryl organic silicon resin |
| CN106117419A (en) * | 2016-07-26 | 2016-11-16 | 立邦涂料（中国）有限公司 | A kind of acrylic acid water dispersoid of hydroxyl and preparation method thereof |
| CN106117419B (en) * | 2016-07-26 | 2018-07-10 | 立邦涂料（中国）有限公司 | A kind of acrylic acid water dispersoid of hydroxyl and preparation method thereof |
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