CN108821993B - Bacteriostatic ultraviolet absorbent, preparation method thereof and application thereof in polymer - Google Patents
Bacteriostatic ultraviolet absorbent, preparation method thereof and application thereof in polymer Download PDFInfo
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- CN108821993B CN108821993B CN201810571565.3A CN201810571565A CN108821993B CN 108821993 B CN108821993 B CN 108821993B CN 201810571565 A CN201810571565 A CN 201810571565A CN 108821993 B CN108821993 B CN 108821993B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
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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
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
Abstract
The invention relates to a bacteriostatic ultraviolet absorbent and a synthesis method thereof. The 2, 4-dihydroxy benzophenone reacts with N-hydroxymethyl benzamide through Friedel-crafts acylation reaction, and then the compound with both antibacterial property and ultraviolet resistance is obtained through centrifugation and alcohol precipitation. The novel ultraviolet absorbent has simple and easy synthesis method and high yield, can make up for the limitation of complicated synthesis process of the traditional ultraviolet absorbent, and can be applied to the preparation of high molecular polymers as a bacteriostatic agent. The bacteriostatic ultraviolet absorbent has very good application prospect in the preparation of high polymer materials.
Description
Technical Field
The invention belongs to the technical field of ultraviolet absorbers. More particularly, the invention relates to a bacteriostatic ultraviolet absorbent containing a UV-O structure, a synthesis method of the ultraviolet absorbent and application of the ultraviolet absorbent in resin synthesis.
Background
It is well known that sunlight is one of the important factors that contribute to the aging degradation of polymers. Although the ultraviolet spectral region (290-400mn) contains less than 5% of solar energy, the sunlight in this wavelength range has enough energy to destroy the chemical bonds in the organic matter, thereby greatly shortening the service life of the organic matter, especially the polymer material. The most widely used means for preventing photo-aging at present is to add an anti-aging agent (e.g., an ultraviolet absorber, a light stabilizer, and a photo-quencher) to a polymer. Wherein the ultraviolet absorbent is an auxiliary agent widely applied to high polymer materials.
Meanwhile, although synthetic polymer materials generally have no mold sensitivity, many products are added with additives such as plasticizers, stabilizers, lubricants, pigments, fillers and the like, and the substances are often damaged by molds, so that the products made of the synthetic polymer materials are aged. The prevention of the invasion of the mold to the polymer material is one of the important subjects studied at home and abroad, and according to a large number of published articles, the mold-proof approach has two aspects: one is a protective coating, and the other is added with a bacteriostatic agent. The coating method, i.e. the shielding method, has various accompanying problems of complex process, easy coating peeling and corrosion to the surface of the base layer, so that researchers generally concentrate on the exploration of the bacteriostatic agent. Therefore, the ultraviolet absorbent with bacteriostatic performance has great application value.
Disclosure of Invention
[ problem to be solved ]
The invention aims to provide a compound with an ultraviolet absorption function.
It is another object of the present invention to provide a process for the preparation of said compounds.
The invention also aims to provide application of the ultraviolet absorbent with bacteriostatic property in resin synthesis.
[ solution ]
The invention is realized by the following technical scheme:
the invention relates to a compound with an ultraviolet absorption function, which has the following specific structural formula:
the invention also relates to a preparation method of the compound, which comprises the following steps:
A. friedel-crafts acylation reaction
In an organic solvent with the weight of reactants of 150-300%, in the presence of a catalyst with the weight of reactants of 10-30%, reacting 2, 4-dihydroxybenzophenone with N-hydroxymethyl benzamide according to the mass ratio of 1: 0.8-1.2, carrying out Friedel-crafts acylation reaction for 1-7 days at the temperature of 10-80 ℃, and then carrying out centrifugal separation to obtain a precipitate;
B. recrystallization
And B, washing the precipitate obtained in the step A with distilled water to be neutral, recrystallizing the washed precipitate in ethanol with the concentration of 30-50% by volume at room temperature for 0.1-0.3 h, carrying out centrifugal separation, washing, and drying in a vacuum drying oven to obtain the 3, 5-di-N-methylbenzamide-2, 4-dihydroxy benzophenone antibacterial ultraviolet absorbent.
In step A, the catalyst is selected from concentrated sulfuric acid, anhydrous aluminum trichloride, a solid acid catalyst, boron trifluoride, stannic chloride, a strongly acidic ion exchange resin or a solid super acid.
In step A, the organic solvent is selected from absolute ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, tert-butyl alcohol, acetone or chloroform.
The bacteriostatic ultraviolet absorbent can be used for products needing bacteriostasis and ultraviolet protection, such as resin.
The resin with the ultraviolet absorption function is a product obtained by carrying out polymerization reaction on 0.5-10 parts by weight of the bacteriostatic ultraviolet absorbent, 10-60 parts by weight of polymerizable monomer, 30-80 parts by weight of organic solvent and 0.5-5.0 parts by weight of initiator at the temperature of 50-90 ℃ for 3-10 hours.
The polymerizable monomer is one or more polymerizable monomers selected from ethyl acrylate, ethyl methacrylate, methacrylic acid, acrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, stearyl acrylate, stearyl methacrylate, vinyl acetate, styrene or a-methyl styrene.
The initiator is azobisisobutyronitrile or benzoyl peroxide.
The organic solvent used in the preparation of the resin having an ultraviolet absorption function is one or more solvents selected from toluene, xylene, acetone, cyclohexanone, methyl isobutyl ketone, ethyl acetate, butyl acetate, n-butanol or ethanol.
[ advantageous effects ]
(1) The compound has the functions of bacteriostasis and ultraviolet resistance, and can be applied to the fields of high polymer materials and the like as a bifunctional compound, such as resin.
(2) The synthesis method of the compound is simple and easy to operate.
Drawings
FIG. 1 shows the UV absorption spectrum of 3, 5-bis-N-methylbenzamide-2, 4-dihydroxybenzophenone, a compound prepared in example 1.
FIG. 2 shows an ultraviolet absorption spectrum of a resin containing the compound 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone prepared in application example 1.
Detailed Description
The following further describes a specific embodiment of the present invention with reference to specific examples.
Example 1 synthesis of 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone in an ethanol-concentrated sulfuric acid system:
21.4g (0.1 mol) of 2, 4-dihydroxybenzophenone, 20.2g (0.1 mol) of N-hydroxymethylbenzamide and 100mL of absolute ethyl alcohol are added into a 250mL three-neck flask equipped with a stirring device, a condensation tube and a thermometer, heated and stirred in an oil bath at 35 ℃, 5mL of concentrated sulfuric acid is added dropwise as a catalyst, the reaction is finished after 3 days, solid-liquid separation is carried out after cooling to room temperature, the obtained solid is repeatedly washed to be neutral by distilled water, recrystallized by absolute ethyl alcohol, then centrifugal separation and washing are carried out again, and drying is carried out in a vacuum drying oven to obtain white powder, namely 3, 5-N-methylbenzamide-2, 4-dihydroxybenzophenone. The yield was 87% calculated according to equation 1.
Equation 1
Wherein M2 is the mass of the product actually obtained, n1 is the amount of the substance of 2, 4-dihydroxybenzophenone, and M2 is the molar molecular weight of the product.
And measuring the infrared spectrum, the nuclear magnetic resonance spectrum and the ultraviolet absorption spectrum of the obtained product.
The infrared spectrum was measured under the following conditions:
using an instrument: U.S. ThermoAVATAR-360
The measurement conditions were as follows: taking a certain amount of vacuum dried samples, grinding and uniformly mixing the vacuum dried samples with dried KBr powder, and tabletting. Immediately using AVATAR-360 infrared absorption spectrometer to measure it at 400cm-1~4000cm-1Infrared absorption in the range
And (3) measuring an infrared spectrum result: IR (KBr, cm)−1）：3270 (υ O-H), 3081 (υ N-H), 1656,1623 (υ C=O).
Nuclear magnetic resonance spectra were measured under the following conditions:
using an instrument: JNM-ECP600, Japan electronic Co., Ltd;
the measurement conditions were as follows: taking a certain amount of vacuum-dried samples, selecting a proper solvent for dissolving, and measuring on a JNMECP600 nuclear magnetic resonance instrument by taking TMS as an internal standard;
1HNMR(DMSO, 600MHz), δ 13.04(s, 1H, O-H), 11.86(s, 1H, O-H), 9.33(t, 1H, N-H), 8.59(t, 1H, N-H), 7.61-7.66 (m, 3H, Ar-H), 7.54(t, 2H, Ar-H), 7.40(s, 1H, Ar-H), 6.09-6.23(m, 4H, -CH2-), 5.74(t, 1H, -CH=), 5.62(t, 1H, -CH=), 4.38(d, 2H, -CH2-), 4.21(d, 2H, -CH2-).
elemental content analysis (calculated): c, 66.31, H, 5.26, O, 21.05, N, 7.36, Found C, 66.29, H, 5.28, O, 21.09, N, 7.36.
From the above analysis, it was confirmed that 3, 5-N-methylbenzamide-2, 4-dihydroxybenzophenone was obtained as white crystals in this example.
The ultraviolet absorption spectrum thereof was measured under the following conditions:
using an instrument: beckman Coulter DU-800
The measurement conditions were as follows: the product was dissolved in N, N-dimethylformamide and made to a concentration of 2X 10-5Mols/liter, determined on a Beckman Coulter DU-800.
Bacteriostatic activity test: the minimum bacteriostatic mass concentration of the 3, 5-di-N-methylbenzamide-2, 4-dihydroxy benzophenone is measured by using escherichia coli and staphylococcus aureus as experimental strains, and the measurement result shows that the minimum bacteriostatic mass concentration of the compound to the escherichia coli and the staphylococcus aureus reaches about 0.03 g/L.
Example 2 synthesis of 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone in the acetone-aluminum trichloride system:
21.4g (0.1 mol) of UV-O, 20.2g (0.1 mol) of N-hydroxymethyl benzamide and 150mL of acetone are added into a 250mL three-neck flask provided with a stirring device, a condensation tube and a thermometer, the mixture is heated and stirred in an oil bath at 35 ℃, 6g of anhydrous aluminum trichloride is added as a catalyst, the reaction is finished after 3 days, the mixture is cooled to room temperature and then subjected to solid-liquid separation, the obtained solid is repeatedly washed to be neutral by distilled water, the obtained solid is recrystallized by absolute ethyl alcohol, then the centrifugal separation and the washing are carried out, and the obtained product is dried in a vacuum drying oven to obtain white powder, namely 3, 5-di-N-methyl benzamide-2, 4-dihydroxy benzophenone. The yield was 85% calculated according to equation 1. The product was characterized in the same way as in example 1.
Example 3 synthesis of 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone in an ethanol-strongly acidic ion exchange resin system:
21.4g (0.1 mol) of 2, 4-dihydroxybenzophenone, 20.2g (0.1 mol) of N-hydroxymethylbenzamide and 100mL of absolute ethyl alcohol were put into a 250mL three-necked flask equipped with a stirrer, a condenser and a thermometer, heated and stirred in a 35 ℃ oil bath, then 5g of a strongly acidic ion exchange resin was added as a catalyst, the reaction was terminated after 3 days, solid-liquid separation was carried out after cooling to room temperature, the obtained solid was repeatedly washed with distilled water to neutrality, recrystallized with absolute ethyl alcohol, centrifuged again, washed, and dried in a vacuum drying oven to obtain white powder, i.e., 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone. The yield was 80% calculated according to equation 1. The product was characterized in the same way as in example 1.
Example 4 synthesis of 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone in a boron trifluoride-isobutanol system:
21.4g (0.1 mol) of 2, 4-dihydroxybenzophenone, 17.12g of N-hydroxymethylbenzamide and 144mL of isobutanol were charged into a 250mL three-necked flask equipped with a stirrer, a condenser and a thermometer, heated and stirred in an oil bath at 80 ℃ and then 5g of boron trifluoride was added as a catalyst, after 1 day, the reaction was terminated, cooled to room temperature and subjected to solid-liquid separation, and the resulting solid was repeatedly washed with distilled water to neutrality, recrystallized with absolute ethanol, centrifuged again, washed and dried in a vacuum drying oven to obtain a white powder, i.e., 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone.
Example 5 synthesis of 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone in a tin tetrachloride-chloroform system:
21.4g (0.1 mol) of 2, 4-dihydroxybenzophenone, 25.68g of N-hydroxymethylbenzamide and 92mL of chloroform were put into a 250mL three-necked flask equipped with a stirrer, a condenser and a thermometer, heated and stirred in a 10 ℃ oil bath, 13g of tin tetrachloride was added as a catalyst, the reaction was terminated after 7 days, cooled to room temperature and subjected to solid-liquid separation, the resulting solid was repeatedly washed with distilled water to neutrality, recrystallized with absolute ethanol, centrifuged again, washed and dried in a vacuum drying oven to obtain a white powder, i.e., 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone.
Application example 1
Preparing acrylic resin containing 3, 5-di-N-methylbenzamide-2, 4-dihydroxy benzophenone:
0.5g of 3, 5-di-N-methylbenzamide-2, 4-dihydroxy benzophenone, 0.5g of azobisisobutyronitrile, 80mL of xylene, 20g of methyl acrylate, 20g of ethyl acrylate and 20g of butyl acrylate are added into a 250mL three-neck round-bottom flask provided with a digital display constant-speed powerful electric stirrer and a condenser, the temperature is raised to 35 ℃ until the initiator is completely dissolved, and then the temperature is raised to 80 ℃ to react for 5 hours, thus finishing the reaction.
The obtained acrylic resin series was measured for ultraviolet absorption spectrum by an ultraviolet spectrophotometer, as shown in FIG. 2. As can be seen from the ultraviolet spectrum of the acrylic resin, after the 3, 5-di-N-methylbenzamide-2, 4-dihydroxybenzophenone is added, the resin has good capability of absorbing ultraviolet rays (275-400 nm).
Bacteriostatic activity test: and naturally curing the obtained resin on the surface of glass, and slicing to determine the bacteriostatic rate. The result shows that when the functional compound 3, 5-di-N-methylbenzamide-2, 4-dihydroxy benzophenone accounts for 0.8 percent of the solid content in the resin, the inhibition rate of the functional compound on escherichia coli and staphylococcus aureus reaches more than 95 percent.
Claims (9)
1. A preparation method of a bacteriostatic ultraviolet absorbent is characterized by comprising the following steps:
A. friedel-crafts acylation reaction
In an organic solvent with the weight of reactants accounting for 10-30%, in the presence of a catalyst with the weight of reactants accounting for 1-10%, reacting 2, 4-dihydroxybenzophenone with N-hydroxymethyl benzamide according to the mass ratio of 1: 0.8-1.2, carrying out Friedel-crafts acylation reaction for 1-7 days at the temperature of 10-80 ℃, and then carrying out centrifugal separation to obtain a precipitate;
B. recrystallization
And B, washing the precipitate obtained in the step A with distilled water to be neutral, recrystallizing the washed precipitate in ethanol with the concentration of 30-50% by volume at room temperature for 0.1-0.3 h, performing centrifugal separation, washing, and drying in a vacuum drying oven to obtain the 3, 5-di-N-methylbenzamide-2, 4-dihydroxy benzophenone antibacterial ultraviolet absorbent.
2. The method according to claim 1, wherein in step A, the catalyst is selected from the group consisting of concentrated sulfuric acid, anhydrous aluminum trichloride, a solid acid catalyst, boron trifluoride, tin tetrachloride, a strongly acidic ion exchange resin, and a solid super acid.
3. The method according to claim 2, wherein in step A, the organic solvent is selected from the group consisting of absolute ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, acetone and chloroform.
4. A bacteriostatic uv-absorber prepared by the method of any one of claims 1 to 3.
5. Use of the bacteriostatic UV absorber prepared by the method of claim 4 in the preparation of a resin with UV absorption function.
6. The use according to claim 5, wherein the resin with ultraviolet absorption function is a product obtained by polymerizing 0.5-10 parts by weight of bacteriostatic ultraviolet absorber, 10-60 parts by weight of polymerizable monomer, 30-80 parts by weight of organic solvent and 0.5-5.0 parts by weight of initiator at 50-90 ℃ for 3-10 hours.
7. Use according to claim 6, characterized in that the polymerizable monomer is one or more polymerizable monomers selected from the group consisting of ethyl acrylate, ethyl methacrylate, methacrylic acid, acrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, stearyl acrylate, stearyl methacrylate, vinyl acetate, styrene or a-methylstyrene.
8. Use according to claim 7, characterized in that the initiator is azobisisobutyronitrile or benzoyl peroxide.
9. Use according to claim 7 or 8, characterized in that the organic solvent is one or more solvents selected from toluene, xylene, acetone, cyclohexanone, methyl isobutyl ketone, ethyl acetate, butyl acetate, n-butanol or ethanol.
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