CN106543428A - Aggretion type UV absorbent containing 0 side bases of UV and preparation method thereof - Google Patents
Aggretion type UV absorbent containing 0 side bases of UV and preparation method thereof Download PDFInfo
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- CN106543428A CN106543428A CN201610920684.6A CN201610920684A CN106543428A CN 106543428 A CN106543428 A CN 106543428A CN 201610920684 A CN201610920684 A CN 201610920684A CN 106543428 A CN106543428 A CN 106543428A
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- aggretion type
- absorbent
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- 0 *CCC(OCCN(CCOC(CCS)=O)Cc(c(O)c(cc1)C(c2ccccc2)=O)c1O)=O Chemical compound *CCC(OCCN(CCOC(CCS)=O)Cc(c(O)c(cc1)C(c2ccccc2)=O)c1O)=O 0.000 description 1
- CFRUEOUXRCWIGG-UHFFFAOYSA-N CCCN(CCO)CC(C(CC=C1C(c2ccccc2)=O)O)=C1O Chemical compound CCCN(CCO)CC(C(CC=C1C(c2ccccc2)=O)O)=C1O CFRUEOUXRCWIGG-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
- C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/02—Polyalkylene oxides
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a kind of preparation method of the aggretion type UV absorbent containing 0 side bases of UV, including：Using 3 (N, N, 2 mercaptopropionic acid ethyl ester amine methyl) there is sulfydryl alkene click-reaction as starting monomer in 2,4 dihydroxy benaophenonels and polyethyleneglycol diacrylate, be subsequently adding photosensitizer, wherein, the addition of photosensitizer for starting monomer gross weight 0.5 1.5%, 3 (N, N, 2 maleimidoproprionic acid ethyl ester amine methyl) mol ratio of 2,4 dihydroxy benaophenonels and polyethyleneglycol diacrylate is 1:1.The invention discloses a kind of aggretion type UV absorbent containing 0 side bases of UV.Contain reactive double bond and sulfydryl in the preparation-obtained aggretion type UV absorber molecules chain of the present invention, can as can response type ultra-violet absorber be applied in macromolecular material；Hydrophilic group is introduced in strand in addition, range of application is further expanded.
Description
Technical field
The invention belongs to pluronic polymer class field, be related to a kind of aggretion type UV absorbent containing UV-0 side bases and its
Preparation method.
Background technology
With the expansion of ozone hole in earth atmosphere, ground ultraviolet radiation intensity is made constantly to increase, to the mankind
And its living environment causes totally unfavorable impact.Macromolecular material for a long time by ultraviolet light radiation can change colour, become fragile,
The accelerated ageing phenomenon such as performance degradation, so that material loses performance.Add UV absorbent in macromolecular material
The too fast aging of material can be obviously improved, so as to extend the service life of material.
Benzophenone ultraviolet absorbent is suitable for because there is preferable UV-resistance in the range of 200～400nm
In various light color articles, it is widely used in plastics, coating, adhesive, rubber Polymer material for defending ultraviolet light old
Change.But low molecule light UV absorbent is decomposed because heat decomposition temperature is low in process using presence in macromolecular material
Loss and it is easy to migration and causes the deficiencies such as bloom, with the continuous renewal of processing method, present in processing and application not
Foot is highlighted, and macromole and polymeric UV absorber research become a kind of current development trend.
The content of the invention
For above-mentioned technical problem, the present invention has designed and developed a kind of aggretion type UV absorbent containing UV-0 side bases
Preparation method.
The present invention has designed and developed a kind of aggretion type UV absorbent containing UV-0 side bases.It is poly- that the present invention is prepared
Contain reactive double bond and sulfydryl in the strand of mould assembly UV absorbent, can be used as can response type aggretion type ultraviolet
Absorbent should may apply to two simultaneously containing hydrophilic segment and oleophylic segment in strand in addition in macromolecular material
In the major part macromolecular material such as parent's property macromolecular material and latex paint, the UV absorbent is further expanded
Range of application.
The present invention provide technical scheme be：
A kind of preparation method of the aggretion type UV absorbent containing UV-0 side bases, including：
Using 3- (N, N,-ethyl 2-mercaptopropionate-amine methyl) -2,4 dihydroxyl benzophenones and two propylene of Polyethylene Glycol
There is sulfydryl-alkene click-reaction as starting monomer in acid esters, be subsequently adding photosensitizer, react 4- with 365nm ultraviolet lights
24h, prepares aggretion type UV absorbent, wherein, the addition of photosensitizer is the 0.5-1.5% of starting monomer gross weight,
3- (N, N, -2- maleimidoproprionic acid ethyl ester-amine methyl) -2,4 dihydroxyl benzophenones and polyethyleneglycol diacrylate
Mol ratio be 1: 1.
Preferably, in the preparation method of the described aggretion type UV absorbent containing UV-0 side bases, 3- (N, N, -2-
Mercaptopropionic acid ethyl ester-amine methyl) synthetic route of -2,4 dihydroxyl benzophenone includes：
Take 3- mercaptopropionic acids, 2,4- dihydroxy -3- (N, N- diethyl alcohol radical methylamino) benzophenone to be dissolved in acetone, plus
Enter DCC and 24-48h is stirred at room temperature, wherein, 3- mercaptopropionic acids and 2,4- dihydroxy -3- (N, N- diethyl alcohol radical methylamino) hexichol first
The mol ratio of ketone is 1: 1 for the mol ratio of 2: 1,3- mercaptopropionic acids and DCC.
Preferably, in the preparation method of the described aggretion type UV absorbent containing UV-0 side bases, 3- (N, N, -2-
Ethoxy-amine methyl) synthetic route of -2,4 dihydroxyl benzophenone includes：
Start to put into paraformaldehyde in batches when diethanolamine is heated 50-70 DEG C, paraformaldehyde is put into per 15min, point
2-6 batches put into, and charging terminates, and are warming up to 60-80 DEG C of reaction 1.0-2.5h, UV-0 are dissolved in organic solvent then, are added to
In above-mentioned reactant liquor, continue reaction 2.5-5h in 60-80 DEG C；Wherein, UV-0 and the mol ratio of diethanolamine are 1: 1.0-2.0；
UV-0 is 1: 1-1.5 with the mol ratio of paraformaldehyde.
Preferably, in the preparation method of the described aggretion type UV absorbent containing UV-0 side bases, the photosensitizer
For 2- hydroxy-2-methyls propiophenone or dimethoxybenzoin.
A kind of aggretion type UV absorbent containing UV-0 side bases, its structural formula is：
N takes natural number, and m is the natural number between 20-45.
Aggretion type UV absorbent containing UV-0 side bases of the present invention and preparation method thereof is preparation-obtained poly-
Contain reactive double bond and sulfydryl in mould assembly UV absorber molecules chain, can as can response type aggretion type ultraviolet inhale
Receiving agent should be in macromolecular material；Amphiphilic be may apply to simultaneously containing hydrophilic segment and oleophylic segment in strand in addition
Property macromolecular material and latex paint etc. major part macromolecular material in, further expand the UV absorbent should
Use scope.
Description of the drawings
Fig. 1 is 1 gained aggretion type UV absorbent P of embodiment1Infrared spectrum.
Fig. 2 is 1 gained aggretion type UV absorbent P of embodiment1Uv absorption spectrogram.
Specific embodiment
The present invention is described in further detail below in conjunction with the accompanying drawings, to make those skilled in the art with reference to description text
Word can be implemented according to this.
The invention provides a kind of preparation method of the aggretion type UV absorbent containing UV-0 side bases, including：Using 3-
(N, N,-ethyl 2-mercaptopropionate-amine methyl) -2,4 dihydroxyl benzophenone is with polyethyleneglycol diacrylate as raw material list
There is sulfydryl-alkene click-reaction in body, be subsequently adding photosensitizer, reacts 4-24h with 365nm ultraviolet lights, prepares polymerization
Type UV absorbent, wherein, the 0.5-1.5% of the addition of photosensitizer for starting monomer gross weight, 3- (N, N, -2- maleoyl
Imido grpup ethyl propionate-amine methyl) mol ratio of -2,4 dihydroxyl benzophenone and polyethyleneglycol diacrylate is 1: 1.
Preferably, in the preparation method of the described aggretion type UV absorbent containing UV-0 side bases, 3- (N, N, -2-
Mercaptopropionic acid ethyl ester-amine methyl) synthetic route of -2,4 dihydroxyl benzophenone includes：
Take 3- mercaptopropionic acids, 2,4- dihydroxy -3- (N, N- diethyl alcohol radical methylamino) benzophenone to be dissolved in acetone, plus
Enter DCC and 24-48h is stirred at room temperature, wherein, 3- mercaptopropionic acids and 2,4- dihydroxy -3- (N, N- diethyl alcohol radical methylamino) hexichol first
The mol ratio of ketone is 1: 1 for the mol ratio of 2: 1,3- mercaptopropionic acids and DCC.
Preferably, in the preparation method of the described aggretion type UV absorbent containing UV-0 side bases, 3- (N, N, -2-
Ethoxy-amine methyl) synthetic route of -2,4 dihydroxyl benzophenone includes：
Start to put into paraformaldehyde in batches when diethanolamine is heated 50-70 DEG C, paraformaldehyde is put into per 15min, point
2-6 batches put into, and charging terminates, and are warming up to 60-80 DEG C of reaction 1.0-2.5h, UV-0 are dissolved in organic solvent then, are added to
In above-mentioned reactant liquor, continue reaction 2.5-5h in 60-80 DEG C；Wherein, UV-0 and the mol ratio of diethanolamine are 1: 1.0-2.0；
UV-0 is 1: 1-1.5 with the mol ratio of paraformaldehyde.
Preferably, in the preparation method of the described aggretion type UV absorbent containing UV-0 side bases, the photosensitizer
For 2- hydroxy-2-methyls propiophenone or dimethoxybenzoin.
The invention provides a kind of aggretion type UV absorbent containing UV-0 side bases, its structural formula is：
N takes natural number, and m is the natural number between 20-45.
Embodiment 1
(1) synthesis of 3- (N, N, -2- ethoxy-amine methyl) -2,4 dihydroxyl benzophenone (HAHBP)
UV-0 is 1: 1 (mol) with the mol ratio of diethanolamine；UV-0 is 1: 1 (mol) with the mol ratio of paraformaldehyde.Will
(diethanolamine excessively can be added the there-necked flask of 2.23g (0.0212mol) diethanolamine input 150mL, to promote reaction to fill
Dividing is carried out), start to put into paraformaldehyde powder in batches when heating 50 DEG C, 0.165g paraformaldehydes are put into per 15min, divides 4 batches
Secondary input, charging terminate, and are warming up to 60 DEG C of insulation 1.0h, 4.54g (0.0212mol) UV-0 are dissolved in 8mL methanol then, are added
To in above-mentioned reactant liquor, 2.5h is incubated in 60 DEG C.Then products in water is removed and removes excessive diethanolamine and paraformaldehyde, it is cold
Lyophilizing dry (vacuum drying), synthetic route is：
(2) synthesis of 3- (N, N,-ethyl 2-mercaptopropionate-amine methyl) -2,4 dihydroxyl benzophenone (EMPAHBP)
In 150mL there-necked flasks, 3- mercaptopropionic acid 1.25g (0.0118mol), 1.655g 2,4- dihydroxy -3- are added
(N, N- diethyl alcohol radical methylamino) benzophenone (0.005mol) is dissolved in the acetone of 30mL, adds 2.43g DCC
(0.0118mol) after 48h being stirred at room temperature, the N of generation is filtered to remove, N- 1,3-Dicyclohexylureas (DCU) obtain filtrate, and water-bath slight fever is removed
Acetone is removed, frozen water is poured into and is washed 3 times, lyophilization obtains orange-yellow crystal.Synthetic route is：
(3) aggretion type UV absorbent P1Synthesis
Take 0.5g (0.001mol) EMPAHBP, 1.0g (0.001mol) polyethyleneglycol diacrylate (1000g/mol),
It is added in the single port bottle of 10ml dichloromethane solutions, adds photosensitizer 2- hydroxy-2-methyl propiophenones, be starting monomer weight
The 0.5% of amount, reacts 24h with 365nm ultraviolet lights in darkroom, removes solvent, and vacuum drying obtains the suction of aggretion type ultraviolet
Receive agent PI.Synthetic route is：
N takes natural number.M is the natural number between 20-45.
Fig. 1 gives aggretion type UV absorbent P prepared by embodiment 11Infrared spectrum.
Fig. 2 gives aggretion type UV absorbent P prepared by embodiment 11Uv absorption spectrogram.
Embodiment 2
(1) synthesis of 3- (N, N, -2- ethoxy-amine methyl) -2,4 dihydroxyl benzophenone (HAHBP)
UV-0: diethanolamine=1: 2.0 (mol)：UV-0: paraformaldehyde=1: 1.5 (mol),
2.23g (0.0212mol) diethanolamine is put into into the there-necked flask of 150mL, starts to throw in batches when heating 70 DEG C
Enter paraformaldehyde powder, 0.2475g paraformaldehydes are put into per 15min, point 4 batches input, charging terminate, and are warming up to 80 DEG C of insulations
Then 2.27g (0.0106mol) UV-0 is dissolved in 15mL methanol by 2.5h, is added in above-mentioned reactant liquor, is incubated 5h in 80 DEG C.
Then products in water is removed goes excessive diethanolamine and paraformaldehyde, lyophilization (to be vacuum dried).Synthetic route is：
(2) synthesis of 3- (N, N,-ethyl 2-mercaptopropionate-amine methyl) -2,4 dihydroxyl benzophenone (EMPAHBP)
In 150mL there-necked flasks, 3- mercaptopropionic acid 1.25g (0.0118mol, 106g/mol), 1.655g 2,4- bis- are added
Hydroxyl -3- (N, N- diethyl alcohol radical methylamino) benzophenone (0.005mol, 331g/mol) is dissolved in the acetone of 30mL, is added
After 2.43gDCC (0.0118mol) is stirred at room temperature 24h, the N of generation is filtered to remove, N- 1,3-Dicyclohexylureas (DCU) obtain filtrate, is steamed
Acetone is removed in distillation, is poured frozen water into and is washed 3 times, and lyophilization obtains orange-yellow crystal.Synthetic route is：
(3) aggretion type UV absorbent PIISynthesis
Take 0.5g (0.001mol) EMPAHBP, 1.0g (0.001mol) polyethyleneglycol diacrylate (1000g/mol),
It is added in the single port bottle of 10ml dichloromethane solutions, adds photosensitizer dimethoxybenzoin, addition is starting monomer weight
1.5%, in darkroom with 365nm ultraviolet lights react 4h, remove solvent, vacuum drying, obtain aggretion type ultra-violet absorption
Agent PII.Synthetic route is：
N is natural number.M is the natural number between 20-45.
Although embodiment of the present invention is disclosed as above, which is not restricted to listed by description and embodiment
With, it can be applied to various suitable the field of the invention completely, for those skilled in the art, can be easily
Other modification is realized, therefore under the general concept limited without departing substantially from claim and equivalency range, the present invention is not limited
In specific details and shown here as the legend with description.
Claims (5)
1. a kind of preparation method of the aggretion type UV absorbent containing UV-0 side bases, it is characterised in that include：
Using 3- (N, N,-ethyl 2-mercaptopropionate-amine methyl) -2,4-DihydroxyBenzophenones and polyethyleneglycol diacrylate
There is sulfydryl-alkene click-reaction as starting monomer, be subsequently adding photosensitizer, 4-24h, system are reacted with 365nm ultraviolet lights
It is standby to obtain aggretion type UV absorbent, wherein, the 0.5-1.5% of the addition of photosensitizer for starting monomer gross weight, 3- (N,
N, -2- maleimidoproprionic acid ethyl ester-amine methyl) -2,4-DihydroxyBenzophenone rubbed with polyethyleneglycol diacrylate
You are than being 1: 1.
2. the aggretion type UV absorbent preparation method of UV-0 side bases is contained as claimed in claim 1, it is characterised in that 3-
The synthetic route of (N, N,-ethyl 2-mercaptopropionate-amine methyl) -2,4-DihydroxyBenzophenone includes：
Take 3- mercaptopropionic acids, 2,4- dihydroxy -3- (N, N- diethyl alcohol radical methylamino) benzophenone to be dissolved in acetone, add
DCC is stirred at room temperature 24-48h, wherein, 3- mercaptopropionic acids and 2,4- dihydroxy -3- (N, N- diethyl alcohol radical methylamino) benzophenone
Mol ratio be the mol ratio of 2: 1,3- mercaptopropionic acids and DCC be 1: 1.
3. the preparation method of the aggretion type UV absorbent of UV-0 side bases is contained as claimed in claim 2, it is characterised in that 3-
The synthetic route of (N, N, -2- ethoxy-amine methyl) -2,4-DihydroxyBenzophenone includes：
Start to put into paraformaldehyde in batches when diethanolamine is heated 50-70 DEG C, paraformaldehyde is put into per 15min, point 2-6 is criticized
Secondary input, charging terminate, and be warming up to 60-80 DEG C of reaction 1.0-2.5h, UV-0 is dissolved in organic solvent then, are added to above-mentioned anti-
In answering liquid, continue reaction 2.5-5h in 60-80 DEG C；Wherein, UV-0 and the mol ratio of diethanolamine are 1: 1.0-2.0；UV-0 with
The mol ratio of paraformaldehyde is 1: 1-1.5.
4. the preparation method of the aggretion type UV absorbent of UV-0 side bases is contained as claimed in claim 1, it is characterised in that institute
Photosensitizer is stated for 2- hydroxy-2-methyls propiophenone or dimethoxybenzoin.
5. a kind of aggretion type UV absorbent containing UV-0 side bases, it is characterised in that its structural formula is：
N takes natural number, and m is the natural number between 20-45.
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| CN201610920684.6A CN106543428B (en) | 2016-10-21 | 2016-10-21 | Aggretion type ultra-violet absorber of the side group containing UV-0 and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105914A (en) * | 2019-05-29 | 2019-08-09 | 罗青菊 | A kind of high grade of transparency organic silicon potting adhesive |
| CN112795282A (en) * | 2020-12-30 | 2021-05-14 | 万博新材料科技（南通）有限公司 | Synthetic method of ultraviolet absorbent for water-based coiled material finish paint |
| CN114989695A (en) * | 2022-04-21 | 2022-09-02 | 宁波宣威彩色世界涂料有限公司 | Water-based environment-friendly odor-free quick-drying floor paint |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105914A (en) * | 2019-05-29 | 2019-08-09 | 罗青菊 | A kind of high grade of transparency organic silicon potting adhesive |
| CN110105914B (en) * | 2019-05-29 | 2022-02-18 | 株洲市美力迪实业有限公司 | High-transparency organic silicon pouring sealant |
| CN112795282A (en) * | 2020-12-30 | 2021-05-14 | 万博新材料科技（南通）有限公司 | Synthetic method of ultraviolet absorbent for water-based coiled material finish paint |
| CN114989695A (en) * | 2022-04-21 | 2022-09-02 | 宁波宣威彩色世界涂料有限公司 | Water-based environment-friendly odor-free quick-drying floor paint |
| CN114989695B (en) * | 2022-04-21 | 2023-02-10 | 宁波宣威彩色世界涂料有限公司 | Water-based environment-friendly odor-free quick-drying floor paint |
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| CN106543428B (en) | 2018-08-03 |
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