CN110003377A - Polymer and preparation method and application - Google Patents
Polymer and preparation method and application Download PDFInfo
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- CN110003377A CN110003377A CN201910214239.1A CN201910214239A CN110003377A CN 110003377 A CN110003377 A CN 110003377A CN 201910214239 A CN201910214239 A CN 201910214239A CN 110003377 A CN110003377 A CN 110003377A
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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
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/24—Homopolymers or copolymers of amides or imides
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
The invention discloses a kind of polymer and preparation method thereof for having UV absorption function, the specific monomer copolymerization using three kinds of different UV absorption wave bands reaches the very big extension of UV absorption range.Achieve the effect that whole wave band ultraviolet shields.The thin polymer film that the present invention obtains has very strong visible light permeability, fluorescence, workability, excellent stability and outstanding ultraviolet screener performance.It can be widely applied to the fields such as aviation, building, agricultural and optical device.
Description
Technical field
The invention belongs to polymer arts, and in particular to a kind of polymer and preparation method thereof for having UV absorption function
And application.
Background technique
Ultraviolet light is a kind of wavelength in 10-400nm range, the black light with very high-energy.Ultraviolet light can segment
For three parts: UVA (320-400nm), UVB (280-320nm) and UVC (100-280 nm).UVC can be obstructed by ozone layer, but
Due to the continuous expansion of Ozone hole in recent years, the UVC intensity for shining upon earth surface is also constantly enhancing.Ultraviolet light
Energy destroys many chemical bonds in material enough, causes photochemical reaction, leads to molecule chain break and compound in material
Decomposition, influence the mechanical performance and service life of material.In addition, fracture strand on living radical can also in air
Oxygen occur photooxidation reaction, make material turn yellow influence its appearance.Have a large number of studies show that, excessive ultraviolet radiation is not only right
Various types of materials has certain negative effect, while different degrees of injury can be also caused to organism, such as cause skin by it is tanned,
Sunburn increases the illness rate of the diseases such as cutaneum carcinoma, cataract.
Polymethyl methacrylate is a kind of important engineering plastics.It has light transmittance height, easy processing, weatherability good
The advantages that, it is widely used in the fields such as aviation, building, agricultural, optical device.However, due to polymethyl methacrylate itself
Ultraviolet screener performance it is very poor, limit its further applying in actual production and life.Exploitation is based on polymethyl
The ultraviolet shielding material of sour methyl esters has become a research hotspot, and the concern by numerous scientific research personnel.
Currently, the method for improving the ultraviolet screener performance of polymethyl methacrylate is usually to adulterate ultraviolet absorber.
Ultraviolet absorber is divided into two classes, and one kind is inorganic ultraviolet absorbent, mainly there is mica, talcum, carbon black and metal oxide
Such as TiO2, CeO, ZnO etc., they have very wide absorption in ultraviolet band, and have good stability.But inorganic ultraviolet absorbent
It is poor with the compatibility of polymethyl methacrylate, the transparency of system is easily reduced after film forming.It can also generate when used for a long time
Phenomena such as migration, bloom, influence the service life of material.Another kind of is organic uv absorbers, mainly includes salicylate
The organic compounds such as class, cinnamate derivative, benzophenone, benzotriazole, triazines and group-substituted acrylonitrile.Organic ultraviolet
Light absorbers can realize that ultraviolet radiation absorption is acted on by absorption effects.They usually have special chromophore and help color
Group, these groups can consumingly absorb the ultraviolet light of a certain wave band, and by the ultraviolet light absorbed be converted into thermal energy, fluorescence or
Person's phosphorescence, and then realize the mesh for absorbing ultraviolet light.
With being widely used for organic uv absorbers, many researchers are by using aliphatic chain to UV absorption
Agent is modified, and improves its compatibility with polymethyl methacrylate.However, the method for traditional physical blending can reduce it is poly-
The mechanical performance of methyl methacrylate, and these small molecule ultraviolet absorbing agents are easy from substrate in high temperature working processes
Middle evolution, reduces the ultraviolet screener performance of finished product, and causes wastage of material.
It is purple how compatibility good, excellent in stability, long service life and ultraviolet screener high-efficient macromolecule are prepared
Outside line shielding material becomes scientific research personnel and endeavours one of the technical issues of solving.
Summary of the invention
The purpose of the present invention is to provide a kind of polymer and preparation method thereof, to solve previous UV absorption polymer
The technical issues of material compatibility is bad, stability is poor, service life is short and ultraviolet screener low efficiency.
Another object of the present invention is to provide a kind of thin polymer film and preparation method thereof, to solve current polymer thin
Film mechanical performance is not good enough, and difficulty of processing is big, the problem that ultraviolet shielded range is not comprehensive enough, efficiency is lower.
In order to achieve the above-mentioned object of the invention, one aspect of the present invention provides a kind of polymer, and the polymer is by methyl-prop
E pioic acid methyl ester, ethylene glycol pyridone acid methacrylate, 4- Methacrylamide yl benzoic acid methyl esters is according to mass ratio 1:
(0.01-10): (0.01-10) is polymerized.
Another aspect of the present invention provide it is a kind of by the Polymer Processing at thin polymer film.
Further aspect of the present invention provides a kind of preparation method of polymer, includes the following steps:
According to mass ratio 1:(0.01-10): (0.01-10) is by methyl methacrylate, ethylene glycol pyridone acid methyl third
Olefin(e) acid ester, 4- Methacrylamide yl benzoic acid methyl esters and micro initiator are dissolved in solvent and carry out polymerization reaction.
Copolymer described in separating-purifying.
Preferably, the temperature of the polymerization reaction is 50-100 DEG C.
Preferably, the reaction time of the polymerization reaction is 2-36h.
Preferably, the initiator includes cyclohexanone peroxide, benzoyl peroxide, lauroyl peroxide, isopropylbenzene mistake
Hydrogen oxide, di-cyclohexylperoxy di-carbonate, potassium peroxydisulfate, ammonium persulfate and azodiisobutyronitrile any of them or more
Kind.
Preferably, the solvent includes any in acetone, ethyl alcohol, methylene chloride, ethyl acetate, tetrahydrofuran and toluene
It is one or more.
Preferably, the protective gas includes one of carbon dioxide, nitrogen and argon gas or a variety of.
Preferably, the separating-purifying processing includes any one in concentration, dissolution-precipitating, washing, centrifugation and suction filtration
Or it is a variety of.
Further aspect of the present invention provides a kind of preparation method of thin polymer film, includes the following steps:
The polymer is taken to be dissolved in solvent；
Acquired solution is poured in container, dry 8-24h, obtains the film under the conditions of 25-60 DEG C.
Preferably, the solution concentration is 1-30wt%.
The polymer is preparing the application in ultraviolet shielded material or device.
Compared with existing product, Inventive polymers have quality performance more uniform, and ultraviolet shielded more efficient, range is more
Comprehensively, the more preferable advantage of mechanical performance.
The thin polymer film has uv-shielding capacity due to being prepared using using the polymer material
More preferably, such as ultraviolet light is almost thus completely shielded within the scope of 200-400nm, i.e., more efficient, and shield ranges are wider, and quality is equal
One, mechanical performance is more preferable, and good performance allows the film to reach identical shielding effect in the case where thinner
Fruit, therefore raw material is more saved, cost is saved, the scope of application is wider.
The preparation method of the polymer, is polymerize using specific monomer, more saves raw material, letter on the premise of ensuring performance
Preparation step is changed, due to being that the uniform processing of single polymers quality gets up also to be more easier, and the polymerization prepared is ultraviolet
Shield effectiveness is higher, and range is wider, and quality is uniform, easy to process, and mechanical performance is more preferable.
The same polymer thin membrane preparation method can save the same of raw material due to using the polymer
When guarantee performance, the thin polymer film prepared is ultraviolet shielded more efficient, and range is wider, and easy to process, quality is uniform, mechanical
Performance is more preferable, easy to process, and the scope of application is wider.
Detailed description of the invention
Present invention will be further explained below with reference to the attached drawings and examples, in attached drawing:
Fig. 1 is the ter-polymers NMR spectrum figure of the embodiment of the present invention；
Fig. 2 is the UV absorption test chart of the ethylene glycol pyridone acid methacrylate of the embodiment of the present invention；
Fig. 3 is the UV absorption test chart of the 4- Methacrylamide yl benzoic acid methyl esters of the embodiment of the present invention；
Fig. 4 is the ultraviolet ray transmissivity test of the thin polymer film and polymethyl methacrylate film of the embodiment of the present invention
Figure.
Specific embodiment
In order to which technical problems, technical solutions and advantageous effects to be solved by the present invention are more clearly understood, below in conjunction with
Embodiment and subordinate list, the present invention will be described in further detail.It should be appreciated that specific embodiment described herein is only used
To explain the present invention, it is not intended to limit the present invention.
On the one hand, the embodiment of the invention provides a kind of polymer.The polymer is by methyl methacrylate, ethylene glycol
Pyridone acid methacrylate, 4- Methacrylamide yl benzoic acid methyl esters is according to mass ratio 1:(0.01-10): (0.01-
10) it is polymerized.The single polymers that copolymerization is formed make the polymer quality uniform, do not need to take into account multiple polymers
Physical and chemical performance, so that the polymer is easy to process, shield effectiveness is higher, therefore only needs less raw material that can reach
To identical performance, raw material has been saved indirectly.
Another aspect of the present invention provides a kind of preparation method of polymer, equation such as following formula:
Using three kinds of monomers by copolyreaction, a step is made, prepares while technique is simplified the polymer
Polymer performance promotion is also obtained, be more convenient further processing, the preparation method of the specific polymer includes as follows
Step:
S01: according to mass ratio 1:(0.01-10): (0.01-10) is by methyl methacrylate, ethylene glycol pyridine ketone acid first
Base acrylate, 4- Methacrylamide yl benzoic acid methyl esters and micro initiator are dissolved in solvent and carry out polymerization reaction.
S02: copolymer described in separating-purifying.
The temperature of polymerization reaction in the specific step S01 is 50-100 DEG C.Choosing this temperature can control polymerization
Reaction rate, will not be because of overheat be caused very much so that reacting uncontrollable development in an appropriate degree fastly, will not be because of temperature
Degree is too low to cause reaction speed excessively slow.
The reaction time of polymerization reaction in the specific step S01 is 2-36h.It is monitored according to different reaction temperatures
After the reaction time is set so that reaction be properly completed.
Initiator in the specific step S01 includes cyclohexanone peroxide, benzoyl peroxide, peroxidating laurel
Acyl, isopropyl benzene hydroperoxide, di-cyclohexylperoxy di-carbonate, potassium peroxydisulfate, ammonium persulfate and azodiisobutyronitrile are wherein appointed
It anticipates one or more.These are all common initiators, and using the different initiator degree of polymerization, changes will occur for polymerization methods, can
Suitable initiator is chosen according to specific requirements.
Solvent in the specific step S01 includes acetone, ethyl alcohol, methylene chloride, ethyl acetate, tetrahydrofuran and first
Any one or more in benzene.Suitable solvent is chosen according to the dissolubility of polymer, the polymer is taken into account molten
The convenience of solution property and purification preparation film forming.
Protective gas in the specific step S01 includes one of carbon dioxide, nitrogen and argon gas or a variety of.Root
Different protective gas can be chosen according to different demands, choose cheap nitrogen in most cases, processability is being needed to want
It can choose that price is higher but performance more preferably argon gas in the case where seeking higher polymer.
Separating-purifying processing in the specific step S02 includes in concentration, dissolution-precipitating, washing, centrifugation and suction filtration
Any one or more.Precipitation ternary is total to after polymer concentration is first more specifically added solvent dissolution in one embodiment
Polymers.
Based on above-mentioned polymer and preparation method thereof, the embodiment of the invention provides a kind of thin polymer films.Due to using
The polymer, the thin polymer film of the embodiment of the present invention has excellent uv-shielding capacity, and can be processed into thinner
Film simultaneously keeps uv-shielding capacity, and practicability is higher, and since quality is uniform, and the technique for processing film forming is also simpler.
The thickness of the thin polymer film of the embodiment of the present invention is generally at 10-1000 μm.While thickness wastes raw material greatly very much
The transmitance of other visible lights is also reduced, thickness is too thin to be not achieved ultraviolet shielded effect.
Further aspect of the present invention provides a kind of preparation method of thin polymer film, includes the following steps:
A01: the polymer is taken to be dissolved in solvent；
A02: acquired solution is poured in container, and dry 8-24h, obtains the film under the conditions of 25-60 DEG C.
Solution concentration described in the specific step A01 is 1-30wt%.The solution of this concentration range can make molten
Liquid has certain viscosity after pouring, too dilute will not can form a film, and will not be too big because of concentration, before causing uniformly to spread out just
Sizing causes film thickness thin uneven.
Solvent described in the specific step A01 includes acetone, ethyl alcohol, methylene chloride, ethyl acetate, tetrahydrofuran
With any one or more in toluene.According in preparation dissolution situation and actual tone of market comprehensively consider solvent
Selection.
Drying temperature in the specific step A02 can make organic solvent volatilize as early as possible, and will not be because of temperature
It is too high so that thin polymer film can not solidify.
This polymeric U shielding properties is good, and various physical characteristics also very excellent benefit can be widely used in preparing
Ultraviolet shielded material or device.
Now in conjunction with specific example, to polymer of the invention and preparation method thereof and thin polymer film and preparation method thereof into
Row is further described.
1. polymer and preparation method thereof
Embodiment 1.1
By 5 grams of methyl methacrylates, 0.1 gram of ethylene glycol pyridone acid methacrylate, 0.1 gram of 4- methacryl
Amido methyl benzoate, 5 milligrams of azodiisobutyronitriles, 30 milliliters of toluene are uniformly mixed under agitation, are led to nitrogen 20 minutes
Sealing system afterwards reacts 12 hours at 90 DEG C.Product is subjected to rotary evaporation, dissolution-precipitation process, obtains pure ternary
Copolymer.
Embodiment 1.2
By 5 grams of methyl methacrylates, 0.5 gram of ethylene glycol pyridone acid methacrylate, 0.5 gram of 4- metering system
Amido benzoic acid methyl esters, 10 milligrams of benzoyl peroxides, 30 milliliters of tetrahydrofurans are uniformly mixed under agitation, lead to argon gas
15 minutes, reaction 12 hours is condensed back at 85 DEG C.Product is subjected to rotary evaporation, washing, suction filtration, drying process, is obtained
Pure terpolymer.
Embodiment 1.3
By 5 grams of methyl methacrylates, 0.5 gram of ethylene glycol pyridone acid methacrylate, 0.5 gram of 4- metering system
Amido benzoic acid methyl esters, 10 milligrams of benzoyl peroxides, 30 milliliters of toluene are uniformly mixed under agitation, and logical argon gas 30 divides
Sealing system after clock reacts 24 hours at 85 DEG C.Product is subjected to rotary evaporation, vacuum drying treatment, obtains pure three
Membered copolymer.
2. thin polymer film and preparation method thereof
Embodiment 2.1
5 grams of terpolymers are dissolved in toluene under 60 DEG C of stirring conditions, solution are poured into glass guide channel, 25
It is 18 hours dry at DEG C, finally film is taken off, obtains whole wave band ultraviolet shielded film.The thin polymer film is carried out purple
Outer absorption test.Test result such as Fig. 4: the UV absorption range of the film covers 200-400nm, and absorption efficiency pole
It is high.
Embodiment 2.2
5 grams of terpolymers are dissolved in toluene under 60 DEG C of stirring conditions, solution are poured into glass guide channel, 40
It is 12 hours dry at DEG C, finally film is taken off, obtains whole wave band ultraviolet shielded film.
Embodiment 2.3
5 grams of terpolymers are dissolved in methylene chloride under 60 DEG C of stirring conditions, solution is poured into glass guide channel,
It is 8 hours dry at 60 DEG C, finally film is taken off, obtains whole wave band ultraviolet shielded film.
3. ultraviolet absorber polymer monomer
Comparative example 1
By 10 mMs of pyridine ketone acid, 20 mMs of 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochlorides,
1 mM of 4-dimethylaminopyridine, 50 milliliters of methylene chloride are uniformly mixed under agitation, and 15 mMs are added after 2 hours
Hydroxyethyl methacrylate reacts 12 hours under room temperature, extracts, obtains ethylene glycol pyridone acid methacrylate monomer.It will
The monomer carries out UV absorption test, test result such as Fig. 2.
Comparative example 2
By 10 mMs of 4-aminobenzoic acid methyl esters, 15 mMs of methacrylic anhydrides, 1 mM of 4- dimethylamino pyrrole
Pyridine, 50 milliliters of methylene chloride uniformly react 12 hours for mixed under room temperature under agitation, extract, obtain 4- methacryl
Amido methyl benzoate monomer.The monomer is subjected to UV absorption test, test result such as Fig. 3.
Embodiment described above is only presently preferred embodiments of the present invention, is not intended to limit the invention, all at this
Made any modifications, equivalent replacements, and improvements etc., should be included in protection model of the invention within the spirit and principle of invention
Within enclosing.
Claims (10)
1. a kind of polymer, it is characterised in that: the polymer is by methyl methacrylate, ethylene glycol pyridone acid methyl propylene
Acid esters, 4- Methacrylamide yl benzoic acid methyl esters are according to mass ratio 1:(0.01-10): (0.01-10) is polymerized.
2. a kind of Polymer Processing as described in claim 1 at thin polymer film.
3. the preparation method of polymer as described in claim 1, which comprises the steps of:
According to mass ratio 1:(0.01-10): (0.01-10) is by methyl methacrylate, ethylene glycol pyridone acids methacrylic acid
Ester, 4- Methacrylamide yl benzoic acid methyl esters and micro initiator are dissolved in solvent and carry out polymerization reaction；
Copolymer described in separating-purifying.
4. the preparation method of polymer as claimed in claim 3, it is characterised in that: the temperature of the polymerization reaction is 50-100
℃。
5. the preparation method of polymer as claimed in claim 3, it is characterised in that: the reaction time of the polymerization reaction is 2-
36h。
6. the preparation method of polymer as claimed in claim 3, it is characterised in that: the initiator includes peroxidating hexamethylene
Ketone, benzoyl peroxide, lauroyl peroxide, isopropyl benzene hydroperoxide, di-cyclohexylperoxy di-carbonate, potassium peroxydisulfate, mistake
Ammonium sulfate and azodiisobutyronitrile any of them or a variety of；And/or
The solvent includes any one or more in acetone, ethyl alcohol, methylene chloride, ethyl acetate, tetrahydrofuran and toluene；
And/or
The protective gas includes one of carbon dioxide, nitrogen and argon gas or a variety of.
7. the preparation method of polymer as claimed in claim 3, it is characterised in that: separating-purifying processing include concentration,
Any one or more in dissolution-precipitating, washing, centrifugation and suction filtration.
8. the preparation method of thin polymer film as claimed in claim 2, which comprises the steps of:
Polymer described in claim 1 is taken to be dissolved in solvent；
Acquired solution is coated and is formed a film, through being dried, thin polymer film.
9. the preparation method of thin polymer film as claimed in claim 8, it is characterised in that: the solution concentration is 1-30wt%.
10. polymer described in claim 2 is preparing the application in ultraviolet shielded material or device.
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| CN201910214239.1A CN110003377B (en) | 2019-03-20 | 2019-03-20 | Polymer, preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113248787A (en) * | 2021-06-21 | 2021-08-13 | 深圳大学 | Plasticizer and preparation method and application thereof |
| CN114621430A (en) * | 2022-04-22 | 2022-06-14 | 深圳大学 | Plasticizer with ultraviolet shielding performance and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004306A1 (en) * | 1986-12-09 | 1988-06-16 | Terumo Kabushiki Kaisha | Ultraviolet-absorptive polymer material |
| US9044623B2 (en) * | 2009-01-27 | 2015-06-02 | Isp Investments Inc. | Polymer-bound UV absorbers in personal care compositions |
| CN105418642A (en) * | 2015-11-03 | 2016-03-23 | 西安交通大学 | Methacrylate fluorescent monomer with thiazolepyridine structure and preparation method thereof |
| CN109438479A (en) * | 2018-10-31 | 2019-03-08 | 深圳市康勋新材科技有限公司 | Ultraviolet absorbing agent and its preparation method and application |
-
2019
- 2019-03-20 CN CN201910214239.1A patent/CN110003377B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004306A1 (en) * | 1986-12-09 | 1988-06-16 | Terumo Kabushiki Kaisha | Ultraviolet-absorptive polymer material |
| US9044623B2 (en) * | 2009-01-27 | 2015-06-02 | Isp Investments Inc. | Polymer-bound UV absorbers in personal care compositions |
| CN105418642A (en) * | 2015-11-03 | 2016-03-23 | 西安交通大学 | Methacrylate fluorescent monomer with thiazolepyridine structure and preparation method thereof |
| CN109438479A (en) * | 2018-10-31 | 2019-03-08 | 深圳市康勋新材科技有限公司 | Ultraviolet absorbing agent and its preparation method and application |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113248787A (en) * | 2021-06-21 | 2021-08-13 | 深圳大学 | Plasticizer and preparation method and application thereof |
| CN114621430A (en) * | 2022-04-22 | 2022-06-14 | 深圳大学 | Plasticizer with ultraviolet shielding performance and preparation method and application thereof |
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| Publication number | Publication date |
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| CN110003377B (en) | 2021-01-12 |
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