CN110283155A - A kind of halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent and preparation method thereof - Google Patents
A kind of halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent and preparation method thereof Download PDFInfo
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- CN110283155A CN110283155A CN201910526502.0A CN201910526502A CN110283155A CN 110283155 A CN110283155 A CN 110283155A CN 201910526502 A CN201910526502 A CN 201910526502A CN 110283155 A CN110283155 A CN 110283155A
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Abstract
The invention discloses halogenated alkoxy Coumarins flame retardant type UV-blue light absorbents and preparation method thereof shown in Formulas I.The halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent has good UV-blue light absorption characteristic, absorption region is broad, ultraviolet light and part high energy blue light can be absorbed, and there is good permeability to the visible light of 480nm or more, and have both flame retarding function, compatibility is good, and machinability is strong, can be used as UV-blue light absorbent for correlative technology field.Halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent synthesis provided by the present invention is simple, easy to operate, is adapted for carrying out industrialized production.Wherein, work as R1When=H, R2=-CH2CH2Br；Work as R1=OCH3When, R2=-CH2CH2Cl or-CH2CH2CH2Cl。
Description
Technical field:
The invention belongs to UV-blue light absorbing material technical fields, and in particular to a kind of halogenated alkoxy Coumarins resistance
Combustion type UV-blue light absorbent and preparation method thereof.
Background technique:
Ultraviolet absorbing agent can ultraviolet light of the selective absorbing in the light sources such as sunlight, then with low-energy radiation
Mode is discharged or is consumed, to implement effective protection to human body and material, is reached and is delayed material aging speed, is improved material and is answered
With the purpose of performance, thus there is biggish practical value in modern industrial production, is widely used to plastics, rubber, sense
The fields such as luminescent material, coating, ink, daily chemical products, textile.
Blue light is most short wavelength, energy highest, the visible light closest to ultraviolet light.It is reported that blue light, especially high energy are blue
Light (400nm-460nm), the crystalline lens that can penetrate human eye reach retina, cause biggish irreversible damage to the eyes of people
Wound, so as to cause eye diseases such as visual fatigue, visual impairment, the dimness of vision, myopia.Here it is cause to discuss warmly extensively at present
" blue light harm ".It is currently being widely used the products such as headlamp, mobile phone, computer, TV and mostly uses LED light source, these are artificial
All there is different degrees of blue ray radiation in light source.It is chronically exposed under blue ray radiation, human eye will necessarily be caused compared with major injury,
Diseases causing blindness can even be induced.Therefore, it is badly in need of the UV-blue light absorbent that exploitation is used for this kind of product, in favor of human eye health.
Although UV-blue light absorbent has obtained the very big attention of researcher, and has carried out extensive research, its product
Kind is still less, and there are many shortcomings, is not able to satisfy the application demand of related fields, and urgent need is done further exploitation and ground
Study carefully.With the fast development of modern science and technology, new diseases field is constantly expanded, and novel photoelectric product is constantly universal, design
It develops the UV-blue light absorbent that new and effective, thermal stability is good, absorption region is wide, selectivity is strong and has become the current technology
The particularly important research topic in one, field, and have broad application prospects.
Summary of the invention:
It is purple the present invention is directed in view of the problems of the existing technology, provide a kind of halogenated alkoxy Coumarins flame retardant type
Outside-blue-light absorbers and its preparation method and application, to overcome above-mentioned the deficiencies in the prior art, the halogenated alkoxy Coumarins
Flame retardant type UV-blue light absorbent has expanded the research and application field of halogenated alkoxy coumarin kind compound, enriches purple
Outside-blue-light absorbers type.
The present invention is achieved by the following technical solutions:
The present invention provides halogenated alkoxy Coumarins flame retardant type UV-blue light absorbents shown in a kind of formula I:
Wherein, work as R1When=H, R2=-CH2CH2Br；Work as R1=OCH3When, R2=-CH2CH2Cl or-CH2CH2CH2Cl。
Halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent proposed by the present invention can pass through conjunction shown in following formula
It is prepared at route:
Wherein, work as R1When=H, R2=-CH2CH2Br；Work as R1=OCH3When, R2=-CH2CH2Cl or-CH2CH2CH2Cl。
The present invention also provides a kind of preparation method of halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent,
The following steps are included: by 3- acetyl group -2H-1- naphtho- [2,1-b] pyran-2-one shown in formula III of the molar ratio for 1:1~1.1
It is dissolved in dehydrated alcohol or anhydrous methanol with substituted benzaldehyde shown in formula II, quickly stirring is lower is added dropwise piperidines, is stirred at reflux anti-
It answers 4~6 hours, after the reaction was completed, is cooled to room temperature, the decompression of obtained solid substance filters, with ethanol washing, with ethanol-acetone
Recrystallization, obtains halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent shown in formula I.
Preferably, the molar ratio of the piperidines and substituted benzaldehyde is 5:1~1.1.
The present invention also provides above-mentioned halogenated alkoxy Coumarins flame retardant type UV-blue light absorbents as ultraviolet-blue
The application of light absorber, the halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent can be used as UV-blue light suction
Agent is received for technical fields such as plastics, coating, ink, display, illumination, glasses, textiles, especially in mobile phone, computer, TV
In terms of equal screen protecting films or spectacles industry, there is potential application foreground.
Halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent proposed by the present invention is in 250-480nm wave band
Existing two apparent absorption bands, peak position is 266-269nm and 401-410nm respectively, and is being greater than 480nm above band without bright
It is aobvious to absorb.Wherein, short-wave absorption band is weak absorbing band, and long wavelength absorption band (310-480nm) shows the strong absorption characteristic in broadband.Cause
This, halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent has good UV-blue light absorption characteristic, absorbs model
Broadness is enclosed, high energy ultraviolet-blue light of the short wave ultraviolet and 310-480nm range that can effectively absorb 250-310nm has
Better assimilation effect and protective action, while also there is good permeability to the visible light of 480nm or more.In addition, because of halogen
For the chlorine or bromine ignition-proof element haveing excellent performance is contained in the molecular structure of alkoxy coumarin compound, so this kind of compound is also
With flame retarding function.
The present invention have it is following the utility model has the advantages that
(1) preparation method of halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent provided by the present invention, behaviour
Make simply, synthesis is convenient, easily controllable；Raw material sources are abundant, and solvent for use recoverable, production cost is low, is adapted for carrying out
Industrialized production.
(2) halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent provided by the present invention has good purple
Outside-blue light absorption characteristics, absorption region is broad, can effectively absorb the short wave ultraviolet and 310-480nm of 250-310nm
The UV-blue light of range has stronger absorbability with the high energy blue light of better assimilation effect, especially 400-450nm
And protective action, while also there is good permeability to the visible light of 480nm or more.Therefore, provided by the present invention halogenated
Alkoxy Coumarins flame retardant type UV-blue light absorbent is selectively good with UV-blue light, protective action is strong, practical value
The features such as high.
(3) halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent provided by the present invention, improving, material is molten
While solution property, the good compatibility of material and machinability are imparted, while because containing in the molecular structure of this kind of compound
The chlorine or bromine ignition-proof element haveing excellent performance, so this kind of compound also has flame retarding function.
(4) present invention has expanded the research and application field of halogenated alkoxy coumarin kind compound, enriches ultraviolet-blue
The type of light absorber.
Detailed description of the invention:
Fig. 1 is that the target product halogenated alkoxy Coumarins flame retardant type UV-blue light that Examples 1 to 3 is prepared is inhaled
Receive ultraviolet-visible absorption spectroscopy figure of the agent in chloroformic solution.
Specific embodiment:
Below with reference to embodiment, technical solution of the present invention is further illustrated, following embodiments be it is illustrative, be not
It is limited, it cannot be limited the scope of protection of the present invention with following embodiments.
Laboratory apparatus and model: Bruker AVANCE-300 nuclear magnetic resonance chemical analyser；Agilent LC/MSD Trap
XCT mass spectrograph；Hitachi U-3900 ultraviolet-uisible spectrophotometer.
Embodiment 1
3- (3- (4- (2- bromine oxethyl) phenyl) -2- acryloyl group) -2H-1- naphtho- [2,1-b] pyran-2-one (IA)
Preparation
In 250mL round-bottomed flask, by 3- acetyl group -2H-1- naphtho- [2,1-b] pyran-2-one (1mmol) and 4- (2-
Bromine oxethyl) benzaldehyde (1mmol) is dissolved in 100mL dehydrated alcohol, piperidines is added dropwise into the solution under fast stirring
0.5mL, and back flow reaction 4 hours under stiring.After the reaction was completed, it is cooled to room temperature, the decompression of obtained solid substance filters, and uses second
Alcohol washing, is recrystallized with ethanol-acetone, obtains yellow solid 3- (3- (4- (2- bromine oxethyl) phenyl) -2- acryloyl group) -
2H-1- naphtho- [2,1-b] pyran-2-one, yield 75%.
Fusing point is 194 DEG C -196 DEG C；1H NMR (300MHz, CDCl3/TMS) δ: 3.69 (t, J=6.3Hz, 2H), 4.37
(t, J=6.3Hz, 2H), 6.97 (d, J=8.7Hz, 2H), 7.53 (d, J=9.0Hz, 1H), 7.61-7.71 (m, 3H), 7.79
(t, J=8.4Hz, 1H), 7.89-8.04 (m, 3H), 8.13 (d, J=9.3Hz, 1H), 8.44 (d, J=8.4Hz, 1H), 9.44
(s,1H).13C NMR(75MHz,CDCl3/TMS)δ:28.64,67.72,114.92,116.46,121.75,122.03,
123.36,126.52,128.29,129.06,129.11,129.69,130.16,130.76,135.97,143.84,144.56,
159.49,160.20,186.17.ESI-MS m/z:449.3(M+H)+。
Embodiment 2
3- (3- (3- methoxyl group -4- (2- chloroethoxy) phenyl) -2- acryloyl group) -2H-1- naphtho- [2,1-b] pyrans -
The preparation of 2- ketone (IB)
In 250mL round-bottomed flask, by 3- acetyl group -2H-1- naphtho- [2,1-b] pyran-2-one (1mmol) and 3- methoxy
Base -4- (2- chloroethoxy) benzaldehyde (1mmol) is dissolved in 100mL anhydrous methanol, is added dropwise under fast stirring into the solution
Piperidines 0.5mL, and back flow reaction 6 hours under stiring.After the reaction was completed, it being cooled to room temperature, the decompression of obtained solid substance filters,
It with ethanol washing, is recrystallized with ethanol-acetone, obtains yellow solid 3- (3- (3- methoxyl group -4- (2- chloroethoxy) phenyl) -
2- acryloyl group) -2H-1- naphtho- [2,1-b] pyran-2-one, yield 73%.
Fusing point is 195 DEG C -197 DEG C；1H NMR(300MHz,CDCl3/ TMS) δ: 3.88 (t, J=6.3Hz, 2H), 3.95
(s, 3H), 4.33 (t, J=6.3Hz, 2H), 6.91 (d, J=8.4Hz, 1H), 7.23-7.29 (m, 2H), 7.50 (d, J=
9.3Hz, 1H), 7.62 (t, J=8.1Hz, 1H), 7.77 (t, J=8.4Hz, 1H), 7.84-8.01 (m, 3H), 8.11 (d, J=
9.0Hz, 1H), 8.41 (d, J=8.4Hz, 1H), 9.41 (s, 1H)13C NMR(75MHz,CDCl3/TMS)δ:41.42,
56.13,68.95,111.25,113.21,113.43,116.56,121.86,122.39,123.43,123.62,126.66,
129.02,129.20,129.24,129.80,130.27,136.14,143.98,144.92,149.74,150.19,156.00,
159.66,186.24.ESI-MS m/z:435.4(M+H)+。
Embodiment 3
3- (3- (3- methoxyl group -4- (3- chloropropanol oxygen radical) phenyl) -2- acryloyl group) -2H-1- naphtho- [2,1-b] pyrans -
The preparation of 2- ketone (IC)
In 250mL round-bottomed flask, by 3- acetyl group -2H-1- naphtho- [2,1-b] pyran-2-one (1mmol) and 3- methoxy
Base -4- (3- chloropropanol oxygen radical) benzaldehyde (1.1mmol) is dissolved in 100mL dehydrated alcohol, is dripped under fast stirring into the solution
Add piperidines 0.5mL, and back flow reaction 5 hours under stiring.After the reaction was completed, it is cooled to room temperature, the decompression of obtained solid substance is taken out
Filter, is recrystallized with ethanol-acetone, obtains yellow solid 3- (3- (3- methoxyl group -4- (3- chloropropanol oxygen radical) phenyl) -2- acryloyl
Base) -2H-1- naphtho- [2,1-b] pyran-2-one, yield 78%.
Fusing point is 170 DEG C -172 DEG C；1H NMR(300MHz,CDCl3/ TMS) δ: 2.32 (m, 2H), 3.79 (t, J=
6.3Hz, 2H), 3.94 (s, 3H), 4.23 (t, J=6.0Hz, 2H), 6.93 (d, J=8.4Hz, 1H), 7.22-7.30 (m, 2H),
7.50 (d, J=9.3Hz, 1H), 7.63 (t, J=8.1Hz, 1H), 7.74 (t, J=8.4Hz, 1H), 7.85-8.00 (m, 3H),
8.11 (d, J=9.0Hz, 1H), 8.42 (d, J=8.4Hz, 1H), 9.41 (s, 1H)13C NMR(75MHz,CDCl3/TMS)δ:
32.08,41.51,56.03,65.46,110.84,112.67,113.22,116.57,121.87,122.04,123.53,
123.88,126.64,128.31,129.18,129.23,129.80,130.28,136.08,143.89,145.18,149.58,
150.92,155.98,159.66,186.25.ESI-MSm/z:449.3(M+H)+。
Embodiment 4
The ultravioletvisible absorption performance test of halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent
The halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent that Examples 1 to 3 is prepared is configured to dense
Degree is 2 × 10-5M chloroformic solution is measured on Hitachi U-3900 ultraviolet-uisible spectrophotometer ultraviolet with 1 centimeter of sample pond
Absorbent properties, as a result as shown in Figure 1.
As shown in Figure 1, (IA, IB have very similar UV, visible light with IC) to three halogenated alkoxy coumarin compounds
Two apparent absorption bands are presented in 250-480nm wave band in absorption spectrum and wider absorption region, and peak position is 266- respectively
269nm and 401-410nm, and absorbed without obvious being greater than 480nm above band.In two absorption bands, short-wave absorption band is
Weak absorbing band, long wavelength absorption band (310-480nm) show the strong absorption characteristic in broadband.The absorption maximum of compound IA, IB and IC
Wavelength is respectively 401nm, 408nm and 410nm, and molar absorption coefficient is respectively 24900,34500 and 35200M-1cm-1.Together
When, in three compounds, the maximum absorption wavelength of IA is significantly less than the maximum absorption wavelength of other two compound IB and IC, and
And its long wavelength absorption band range is 310-460nm, compared with IB and IC, hence it is evident that blue shift, this is related with its molecular structure.
The above results show that halogenated alkoxy coumarin kind compound (IA, IB and IC) all has good UV-blue light
Absorption characteristic, absorption region is broad, can effectively absorb the short wave ultraviolet of 250-310nm and the height of 310-480nm range
Energy UV-blue light has stronger absorbability with the high energy blue light of better assimilation effect, especially 400-450nm and prevents
Shield effect, while also there is good permeability to the visible light of 480nm or more.In addition, this kind of compound is because in molecular structure
There is flame retarding function containing the chlorine or bromine ignition-proof element haveing excellent performance.Therefore, halogenated alkoxy tonka-bean provided by the present invention
Chlorins compound can be used as UV-blue light absorbent for technologies such as plastics, coating, ink, display, illumination, glasses, textiles
Field has potential application foreground especially in terms of the screen protecting films such as mobile phone, computer, TV or spectacles industry.
Above-listed detailed description is illustrating for one of present invention possible embodiments, and the embodiment is not to limit
The scope of the patents of the invention, all equivalence enforcements or change without departing from carried out by the present invention, is intended to be limited solely by the scope of the patents of this case
In.
Claims (6)
1. halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent shown in a kind of formula I:
Wherein, work as R1When=H, R2=-CH2CH2Br；Work as R1=OCH3When, R2=-CH2CH2Cl or-CH2CH2CH2Cl。
2. a kind of preparation method of halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent described in claim 1,
It is characterized in that, comprising the following steps: be 3- acetyl group -2H-1- naphtho- [2,1-b] pyran-2-one of 1:1~1.1 by molar ratio
It is dissolved in dehydrated alcohol or anhydrous methanol with substituted benzaldehyde shown in formula II, quickly stirring is lower is added dropwise piperidines, is stirred at reflux anti-
It answers 4~6 hours, after the reaction was completed, is cooled to room temperature, the decompression of obtained solid substance filters, and washs, recrystallization, obtains target production
Object；
Wherein, work as R1When=H, R2=-CH2CH2Br；Work as R1=OCH3When, R2=-CH2CH2Cl or-CH2CH2CH2Cl。
3. the preparation method of halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent according to claim 2,
It is characterized in that, the molar ratio of the piperidines and substituted benzaldehyde is 5:1~1.1.
4. halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent described in claim 1 is ultraviolet-blue as flame retardant type
The application of light absorber.
5. halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent according to claim 4 is as flame retardant type purple
Outside-blue-light absorbers application, which is characterized in that the halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent
Plastics, coating, ink, display, illumination, glasses and textile are used for as flame retardant type UV-blue light absorbent.
6. halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent according to claim 5 is as flame retardant type purple
Outside-blue-light absorbers application, which is characterized in that the halogenated alkoxy Coumarins flame retardant type UV-blue light absorbent
Screen protecting film is used for as flame retardant type UV-blue light absorbent.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101809116A (en) * | 2007-08-17 | 2010-08-18 | 巴斯夫欧洲公司 | Halogen-containing perylenetetracarboxylic acid derivatives and the use thereof |
| CN108191624A (en) * | 2017-12-15 | 2018-06-22 | 广东省石油与精细化工研究院 | A kind of UV-blue light absorbent and UV-blue light absorbing material |
-
2019
- 2019-06-18 CN CN201910526502.0A patent/CN110283155B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101809116A (en) * | 2007-08-17 | 2010-08-18 | 巴斯夫欧洲公司 | Halogen-containing perylenetetracarboxylic acid derivatives and the use thereof |
| CN108191624A (en) * | 2017-12-15 | 2018-06-22 | 广东省石油与精细化工研究院 | A kind of UV-blue light absorbent and UV-blue light absorbing material |
Non-Patent Citations (2)
| Title |
|---|
| YI-FENG SUN ET AL.: "Solid-state Fluorescence Emission and Second-Order Nonlinear Optical Properties of Coumarin-based Fluorophores", 《J FLUORESC》 * |
| 孔德玉 等: "蓝光吸收剂在PC中的应用探究", 《工程塑料应用》 * |
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