CN108821993A - A kind of antibacterial type ultraviolet absorbing agent, preparation method and application in the polymer - Google Patents
A kind of antibacterial type ultraviolet absorbing agent, preparation method and application in the polymer Download PDFInfo
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- CN108821993A CN108821993A CN201810571565.3A CN201810571565A CN108821993A CN 108821993 A CN108821993 A CN 108821993A CN 201810571565 A CN201810571565 A CN 201810571565A CN 108821993 A CN108821993 A CN 108821993A
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- ultraviolet absorbing
- preparation
- absorbing agent
- type ultraviolet
- antibacterial type
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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 present invention relates to a kind of antibacterial type ultraviolet absorbing agent and its synthetic methods.2,4-DihydroxyBenzophenone react with N- methylol benzamide by friedel-crafts acylation, is then passed through and is centrifuged, and alcohol precipitation is had antibiotic property and the difunctional compound of uvioresistant simultaneously.New ultra-violet light absorber synthetic method of the invention is simple and easy, yield is high, can overcome the disadvantages that the cumbersome limitation of conventional ultra-violet absorbent synthesis technology, while can also be applied in the preparation of high molecular polymer as bacteriostatic agent.Antibacterial type ultraviolet absorbing agent of the invention has very good application prospect in the preparation of high molecular material.
Description
Technical field
The invention belongs to the technical fields of ultraviolet absorbing agent.More specifically, the present invention relates to one kind to contain UV-O structure
Antibacterial type ultraviolet absorbing agent, further relate to the synthetic method of the ultraviolet absorbing agent and its application in resins synthesis.
Background technique
It is well known that sunlight is one of an important factor for leading to polymer degradation with aging.Although ultraviolet spectra area (290-
400mn) comprising the solar energy less than 5%, but the sunlight in this wave-length coverage has in enough energy damages organic matters
Chemical bond, to greatly shorten the service life of organic matter especially high molecular material.It is most popular at present anti-
Light aging means are that age resister is added in high molecular polymer（Ultraviolet absorbing agent, light stabilizer, optical quenching agent etc.）.Its
Middle-ultraviolet lamp absorbent is a kind of auxiliary agent for being widely used in high molecular material.
Meanwhile high molecular material although typically no mould sensitivity is synthesized, but many products are due to added with plasticizer, steady
Determine the additives such as agent, lubricant, pigment, filler, and this substance is often by the destruction of mould, so as to cause synthesis high score
Aging occurs for sub- material product.Infringement of the mould to high molecular material is prevented, has been one of the important topic studied both at home and abroad, root
Apparently, mould proof approach substantially has two aspects to article according to a large amount of the sixth of the twelve Earthly Branches through delivering：One is protective coating, another antibacterial to add
Agent.Coating, that is, screen method, this method are easily peeled off and are asked the various associations of the corrosion of substrate surface because still having complex process, coating
Topic needs to consider, so general Study person mostly concentrates on the exploration of bacteriostatic agent.Therefore, ultraviolet absorbing agent is assigned with biocidal property
Can there will be great application value.
Summary of the invention
[technical problems to be solved]
The object of the present invention is to provide a kind of compounds with UV absorption function.
It is a further object to provide the preparation methods of the compound.
It is a further object to provide the ultraviolet absorbing agents with bacteriostasis property in resins synthesis
Using.
[technical solution]
The present invention is achieved through the following technical solutions：
The present invention relates to a kind of compound with UV absorption function, concrete structure formula is as follows：
The invention further relates to the preparation method of the compound, the step of preparation method, is as follows：
A, friedel-crafts acylation
In in terms of reactant weight 150~300% organic solvent, the catalyst in terms of reactant weight 10~30% is deposited
Under, 2,4-DihydroxyBenzophenone and N- methylol benzamide reactant are according to mass ratio 1：0.8 ~ 1.2, temperature 10 ~
It is carried out friedel-crafts acylation 1 ~ 7 day at 80 DEG C, is then centrifuged for a kind of isolated sediment；
B, it recrystallizes
The sediment that step A is obtained is washed with distilled water to neutrality, then allows washing precipitate in concentration by volume 30~50%
Ethyl alcohol in, recrystallize 0.1~0.3h at room temperature, then be centrifugated, wash, dry in a vacuum drying oven, obtain 3,5-
Two-N-methyl-benzamides -2,4 dihydroxyl benzophenone antibacterial type ultraviolet absorbing agent.
In step, the catalyst be selected from the concentrated sulfuric acid, aluminum trichloride (anhydrous), solid acid catalyst, boron trifluoride,
Tin tetrachloride, strong-acid ion exchange resin or solid super-strong acid.
In step, the organic solvent is selected from dehydrated alcohol, normal propyl alcohol, isopropanol, n-butanol, isobutanol, tertiary fourth
Alcohol, acetone or chloroform.
The antibacterial type ultraviolet absorbing agent can be used in needing antibacterial and antiultraviolet product, such as resin.
The resin with UV absorption function be the antibacterial type ultraviolet absorbing agent as described in 0.5~10 parts by weight,
10~60 parts by weight polymerisable monomers, 30-80 weight parts organic solvent and 0.5~5.0 parts by weight initiator, in temperature 50-90
Polymerization reaction 3-10 hours obtained product is carried out under conditions of DEG C.
The polymerisable monomer be it is one or more selected from ethyl acrylate, ethyl methacrylate, methacrylic acid,
Acrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, octadecyl acrylate, methyl
Octadecyl acrylate, vinyl acetate, styrene or a- methyl styrene polymerisable monomer.
The initiator is azodiisobutyronitrile or benzoyl peroxide.
Organic solvent used is one or more selected from toluene, diformazan when the preparation resin with UV absorption function
Benzene, acetone, cyclohexanone, hexone, ethyl acetate, butyl acetate, n-butanol or ethyl alcohol solvent.
[beneficial effect]
（1）Compound has antibacterial and anti-ultraviolet function simultaneously, can apply and macromolecule material as a kind of dual-function compound
The fields such as material, such as resin.
（2）The synthetic method of compound is simple, easily operated.
Detailed description of the invention
Fig. 1 is bis--N-methyl-benzamide of compound 3,5- -2,4 dihydroxyl benzophenone purple prepared by embodiment 1
Outer absorption spectrum.
Fig. 2 contains bis--N-methyl-benzamide of compound 3,5- -2,4- dihydroxy hexichol for prepared by Application Example 1
The ultra-violet absorption spectrum of ketone resin.
Specific embodiment
The specific technical solution of the present invention is further described combined with specific embodiments below.
Embodiment 1 synthesizes bis--N-methyl-benzamide of 3,5- -2,4- dihydroxy hexichol in ethyl alcohol-concentrated sulfuric acid system
Ketone：
21.4g is added in the 250mL three-necked flask for being equipped with agitating device, condenser pipe and thermometer（0.1mol）2,4- dihydroxy
Benzophenone, 20.2g（0.1mol）N- methylol benzamide and 100mL dehydrated alcohol, the heating stirring in 35 DEG C of oil baths, so
The concentrated sulfuric acid of 5mL is added dropwise afterwards as catalyst, reaction terminates after 3 days, is separated by solid-liquid separation after being cooled to room temperature, and use distilled water
Washing obtained solid is recrystallized to neutrality with dehydrated alcohol repeatedly, then is centrifugated, and is washed, is dried, obtain in a vacuum drying oven
White powder, i.e. 3,5-N- methyl benzamide -2,4-DihydroxyBenzophenone.Calculating yield according to formula 1 is 87%.
Formula 1
Wherein, m2 is real income product quality, and n1 is the amount of the substance of 2,4-DihydroxyBenzophenone, and M2 is mole of product
Molecular weight.
Measure infrared spectroscopy, nuclear magnetic resoance spectrum and the ultra-violet absorption spectrum of products obtained therefrom.
Infrared spectroscopy is determined under the following conditions：
Use instrument：U.S. ThermoAVATAR-360
Determination condition：Sample after taking a certain amount of vacuum drying mixes, tabletting with dry KBr powder mull.It uses immediately
AVATAR-360 infrared absorption spectrometer measures it in 400cm-1~4000cm-1Infrared absorption in range
Measure the results of FT-IR：IR（KBr, cm−1）：3270 (υ O-H), 3081 (υ N-H), 1656,1623 (υ C=O).
Nuclear magnetic resoance spectrum is determined under the following conditions：
Use instrument：Jeol Ltd. JNM-ECP600；
Determination condition：Sample after taking a certain amount of vacuum drying, after selecting solvent appropriate to dissolve, using TMS as internal standard,
It is measured in JNMECP600 Nuclear Magnetic Resonance；
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-).
Constituent content analysis value（Calculated value）：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.
By above-mentioned analysis it was determined that the white crystal that the present embodiment is prepared is 3,5-N- methyl benzamide -2,4-
Dihydroxy benaophenonel.
Its ultra-violet absorption spectrum is determined under the following conditions：
Use instrument：Beckman Coulter DU-800
Determination condition：It is 2 × 10 that product, which is melted into N,N-dimethylformamide, and is made into concentration-5Mol/L, in Beckman
It is measured on Coulter DU-800.
Biocidal property experiment：It is experimental strain with Escherichia coli and staphylococcus aureus, to 3,5-, bis--N- toluyl
Amine -2,4-DihydroxyBenzophenone minimum-bacteriostat mass concentration is measured, and measurement result is shown, the compound is to large intestine bar
The minimum-bacteriostat mass concentration of bacterium and staphylococcus aureus has reached 0.03g/L or so.
Embodiment 2 is in acetone --- synthesis 3,5- bis--N-methyl-benzamide -2,4- dihydroxy in alchlor system
Base benzophenone：
21.4g is added in the 250mL three-necked flask for being equipped with agitating device, condenser pipe and thermometer（0.1mol）UV-O,20.2g
（0.1mol）N- methylol benzamide and 150mL acetone, the heating stirring in 35 DEG C of oil baths are added 6g aluminum trichloride (anhydrous) and do
Catalyst, reaction terminates after 3 days, is separated by solid-liquid separation after being cooled to room temperature, and wash obtained solid repeatedly into distilled water
Property, it is recrystallized, then be centrifugated, is washed with dehydrated alcohol, dried in a vacuum drying oven, obtain white powder, i.e., 3, bis--N- of 5-
Methyl benzamide -2,4 dihydroxyl benzophenone.Calculating yield according to formula 1 is 85%.The characterizing method and embodiment of product
1 is identical.
Embodiment 3 is in ethyl alcohol --- bis--N-methyl-benzamide of 3,5--is synthesized in strong-acid ion exchange resin system
2,4 dihydroxyl benzophenone：
21.4g is added in the 250mL three-necked flask for being equipped with agitating device, condenser pipe and thermometer（0.1mol）2,4- dihydroxy
Benzophenone, 20.2g（0.1mol）N- methylol benzamide and 100ml dehydrated alcohol, the heating stirring in 35 DEG C of oil baths, so
5g strong-acid ion exchange resin is added afterwards as catalyst, reaction terminates after 3 days, it is separated by solid-liquid separation after being cooled to room temperature,
And wash obtained solid repeatedly with distilled water and recrystallized to neutrality with dehydrated alcohol, then be centrifugated, it washs, is being dried in vacuo
It is dry in case, obtain white powder, i.e. 3,5-, bis--N-methyl-benzamide -2,4-DihydroxyBenzophenone.It is calculated according to formula 1
Yield is 80%.The characterizing method of product is same as Example 1.
Embodiment 4 is in boron trifluoride --- bis--N-methyl-benzamide of 3,5- -2,4- dihydroxy is synthesized in isobutanol system
Base benzophenone：
21.4g is added in the 250mL three-necked flask for being equipped with agitating device, condenser pipe and thermometer（0.1mol）2,4- dihydroxy
Benzophenone, 17.12gN- methylol benzamide and 144ml isobutanol, the heating stirring in 80 DEG C of oil baths, are then added 5g
Boron trifluoride is as catalyst, and reaction terminates after 1 day, is separated by solid-liquid separation after being cooled to room temperature, and washed repeatedly with distilled water
Obtained solid is recrystallized to neutrality with dehydrated alcohol, then is centrifugated, and washing is dried in a vacuum drying oven, obtains white powder
End, i.e. 3,5-, bis--N-methyl-benzamide -2,4-DihydroxyBenzophenone.
Embodiment 5 is in tin tetrachloride --- bis--N-methyl-benzamide of 3,5- -2,4- dihydroxy is synthesized in chloroform system
Benzophenone：
21.4g is added in the 250mL three-necked flask for being equipped with agitating device, condenser pipe and thermometer（0.1mol）2,4- dihydroxy
Then 13g tetra- is added in benzophenone, 25.68gN- methylol benzamide and 92ml chloroform, the heating stirring in 10 DEG C of oil baths
Stannic chloride is as catalyst, and reaction terminates after 7 days, is separated by solid-liquid separation after being cooled to room temperature, and wash institute repeatedly with distilled water
It obtains solid to be recrystallized to neutrality with dehydrated alcohol, then is centrifugated, wash, dry in a vacuum drying oven, obtain white powder,
That is bis--N-methyl-benzamide of 3,5- -2,4 dihydroxyl benzophenone.
Application Example 1
Containing the preparation of bis--N-methyl-benzamide of 3,5- -2,4 dihydroxyl benzophenone acrylic resin：
0.5g 3,5- bis--is added in the 250mL three neck round bottom flask equipped with digital display constant speed powerful motor blender and condenser pipe
N-methyl-benzamide -2,4-DihydroxyBenzophenone, 0.5g azodiisobutyronitrile, 80ml dimethylbenzene, 20g methyl acrylate,
20g ethyl acrylate, 20g butyl acrylate rise to 35 DEG C and are completely dissolved to initiator, then heat to 80 DEG C of reaction 5h knots
Beam.
Resulting serial acrylic resin ultraviolet specrophotometer is surveyed into ultra-violet absorption spectrum, as shown in Figure 2.By propylene
It is found that after addition 3,5-, bis--N-methyl-benzamide -2,4-DihydroxyBenzophenone, resin has the ultraviolet spectra of acid resin
Good absorption ultraviolet light（275-400nm）Ability.
Biocidal property experiment：By resulting resin after glass surface spontaneous curing, slice carries out bacteriostasis rate measurement.As a result table
Bright, when functional compounds 3, bis--N-methyl-benzamide of 5- -2,4-DihydroxyBenzophenone accounts for 0.8% of solid content in resin
When, 95% or more has been reached to the inhibiting rate of Escherichia coli and staphylococcus aureus.
Claims (9)
1. a kind of antibacterial type ultraviolet absorbing agent, it is characterised in that it has following chemical structural formula（I）：
（I）.
2. the preparation method of antibacterial type ultraviolet absorbing agent described in a kind of claim 1, which is characterized in that include the following steps：
A, friedel-crafts acylation
In in terms of reactant weight 10~30% organic solvent, in the presence of in terms of reactant weight 1~10% catalyst
Under, 2,4-DihydroxyBenzophenone and N- methylol benzamide reactant are according to mass ratio 1：0.8 ~ 1.2 in temperature 10 ~ 80
It is carried out friedel-crafts acylation 1 ~ 7 day at DEG C, is then centrifuged for a kind of isolated sediment；
B, it recrystallizes
The sediment that step A is obtained is washed with distilled water to neutrality, then allows washing precipitate in concentration by volume 30~50%
Ethyl alcohol in recrystallize 0.1~0.3h at room temperature, then be centrifugated, wash, dry in a vacuum drying oven, obtain 3,5-
Two-N-methyl-benzamides -2,4 dihydroxyl benzophenone antibacterial type ultraviolet absorbing agent.
3. preparation method according to claim 2, it is characterised in that in step, the catalyst be selected from the concentrated sulfuric acid,
Aluminum trichloride (anhydrous), solid acid catalyst, boron trifluoride, tin tetrachloride, strong-acid ion exchange resin or solid super-strong acid.
4. preparation method according to claim 2, it is characterised in that in step, the organic solvent is selected from anhydrous
Ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, isobutanol, the tert-butyl alcohol, acetone or chloroform.
5. the antibacterial type ultraviolet absorbing agent that preparation method described in a kind of any one of claim 2-4 claim is prepared
Purposes in the resin that preparation has UV absorption function.
6. purposes according to claim 5, it is characterised in that the resin with UV absorption function is by 0.5~10
Parts by weight antibacterial type ultraviolet absorbing agent, 10~60 parts by weight polymerisable monomers, 30-80 weight parts organic solvent and 0.5~5.0
Parts by weight initiator carries out polymerization reaction 3-10 hours obtained product under conditions of 50-90 DEG C of temperature.
7. purposes according to claim 6, it is characterised in that the polymerisable monomer is one or more selected from propylene
Acetoacetic ester, ethyl methacrylate, methacrylic acid, acrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate,
Butyl methacrylate, octadecyl acrylate, octadecyl methacrylate, vinyl acetate, styrene or a- methyl styrene
Polymerisable monomer.
8. purposes according to claim 7, it is characterised in that the initiator is azodiisobutyronitrile or benzoyl peroxide
Formyl.
9. purposes according to claim 7 or 8, it is characterised in that the organic solvent is one or more selected from first
Benzene, dimethylbenzene, acetone, cyclohexanone, hexone, ethyl acetate, butyl acetate, n-butanol or ethyl alcohol solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810571565.3A CN108821993B (en) | 2018-06-06 | 2018-06-06 | Bacteriostatic ultraviolet absorbent, preparation method thereof and application thereof in polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810571565.3A CN108821993B (en) | 2018-06-06 | 2018-06-06 | Bacteriostatic ultraviolet absorbent, preparation method thereof and application thereof in polymer |
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| Publication Number | Publication Date |
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| CN108821993A true CN108821993A (en) | 2018-11-16 |
| CN108821993B CN108821993B (en) | 2021-05-21 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1023834A1 (en) * | 1999-01-29 | 2000-08-02 | American Cyanamid Company | Fungicidal mixtures |
| CN105348131A (en) * | 2015-12-03 | 2016-02-24 | 中国海洋大学 | Reaction type ultraviolet light absorber as well as a preparation method and application thereof |
-
2018
- 2018-06-06 CN CN201810571565.3A patent/CN108821993B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1023834A1 (en) * | 1999-01-29 | 2000-08-02 | American Cyanamid Company | Fungicidal mixtures |
| CN105348131A (en) * | 2015-12-03 | 2016-02-24 | 中国海洋大学 | Reaction type ultraviolet light absorber as well as a preparation method and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| MINGLI SHAN，等: "A strategy of integrating ultraviolet absorption and crosslinking in a single molecule: DFT calculation and experimental", 《JOURNAL OF MOLECULAR STRUCTURE》 * |
| 上海市合成树脂研究所: "《国外稳定剂发展概况 热稳定剂、抗氧剂、紫外线稳定剂》", 30 November 1975, 上海科学技术情报研究所 * |
| 化工部合成材料研究院: "《聚合物防老化实用手册》", 30 June 1999, 化学工业出版社 * |
| 林艳，等: "二苯甲酮类化合物的合成及抗真菌活性", 《中国实验方剂学杂志》 * |
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