CN106632102A - Application of hyper branched polytriazole in detection of diarylamines antioxidant - Google Patents
Application of hyper branched polytriazole in detection of diarylamines antioxidant Download PDFInfo
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- CN106632102A CN106632102A CN201610824859.3A CN201610824859A CN106632102A CN 106632102 A CN106632102 A CN 106632102A CN 201610824859 A CN201610824859 A CN 201610824859A CN 106632102 A CN106632102 A CN 106632102A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
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Abstract
The invention belongs to the field of a polymer functional material, and discloses an application of hyper branched polytriazole in detection of a diarylamines antioxidant. The hyper-branched polytriazole comprises a structure shown in a formula (I), wherein, R1 and R3 are same or different organic radicals, R2 is a connecting functional group, Fx is fluorine atoms connected on phenyl ring, x expresses number of fluorine atoms, and x is an integer between 2-4. Compared with a current detection analysis method in the prior art, hyper branched polytriazole as a fluorescence chemical sensor does not require a complex pretreatment process of a to-be-processed object, an extremely few of sample is required, which requires obvious fluorescence signal response (the detection limit is as low as 54 nM), detection sensitivity is high, and selectivity is good, interference due to other substances in complex environment is not generated, and the hyper branched polytriazole has the advantages of easy carrying, low cost, rapidity, and accuracy; and can be used for a real-time, on-site, high-selectivity and high-sensitivity analysis.
Description
Technical field
The invention belongs to polymer-function material field, more particularly to a kind of hyperbranched poly triazole is in detection diarylamines
Application in age resistor, with high selectivity and sensitivity.
Background technology
There is in use the phenomenons such as face checking, whiting and physical and mechanical properties decline, system in rubber, plastic products
Referred to as " aging ".Permanent for product of rubber and plastic effectively uses, and needs add (allocating into) in sizing material, and some can suppress above-mentioned
The material that aging phenomenon occurs, it is this kind of with the material for being capable of delaying aging to increase the service life and storage period, it is referred to as
For age resistor.Age resistor can be divided into by its structure：Amines antioxidants, phenol antiager and other class age resistor.Wherein, amine is prevented
The protection effect (effect) of old agent is excellent, and price is relatively cheap, and consumption figure is maximum, it has also become the dominant type of age resistor.
In recent years, in order to pursue the high-performance and durability of product of rubber and plastic, the kind of age resistor newly developed in product formula
Class is more, and match ratio is more complicated.Can it is easy in a cost-effective manner, quickly and accurately analyze age resistor or species
Ownership, for exploitation, to prepare new premium quality product significant.On the other hand, amines antioxidants, especially diaryl
, there is strong carcinogenic risk in amine, although at present usage amount is huge, but is gradually forbidden in association areas such as food, medical treatment
Use.Fast and accurately detect the product of rubber and plastic containing this kind of age resistor, so as to avoid it is unsafe use, with important
Life and health meaning.
At present, it is for organic solvent using additive in rubber to the basic skills of product of rubber and plastic age resistor analysis
Dissolving sex differernce it is different with heat-resisting property separated, concentrate, be then analyzed.Analysis is generally infrared using Fourier,
The instruments such as high performance liquid chromatography, gas chromatography-mass spectrography are carried out.Although this analysis can provide accurate data, instrument
Device involves great expense, while the preparation of samples process complexity before test is analyzed, and can not be real-time, on the spot, quickly make detection.
It is inexpensive and the chemical sensor for being based on fluorescent material possesses portable just, it is sensitive, the advantages of quick, can be real-time, on the spot right
Tested substance makes accurately detection.Therefore development is based on the age resistor chemical sensor of fluorescent dye, not only with great
Scientific value, with more huge actual application prospect.
The content of the invention
In order to overcome the shortcoming and deficiency of above-mentioned prior art, it is an object of the invention to provide a kind of hyperbranched poly triazole
Application in detection diarylamines age resistor.The chemical sensor prepared using the hyperbranched poly triazole, to diaryl amine
Class age resistor shows the selectivity of superelevation and sensitivity, without the need for carrying out the pretreatment of complexity to being detected sample, with real-time,
On the spot, it is micro, quickly, the function of diarylamines age resistor accurately whether is added in analysis product of rubber and plastic.
The purpose of the present invention is realized by following proposal：
A kind of application of hyperbranched poly triazole in detection diarylamines age resistor, the hyperbranched poly triazole has formula
(I) structure shown in：
In formula (I), R1, R3For identical or different organic group, R2To connect functional group, FxTo be connected on phenyl ring
Fluorine atom, x represents the number of F atom, and x is 2～4 integer.
Wherein, R1, R3One kind in following chemical structural formula 1～18；R2Appointing in following structural formula 19～22
Meaning is a kind of；
Wherein, * represents the position of substitution.
Application of the hyperbranched poly triazole in detection diarylamines age resistor, specifically includes following steps：
(1) mixed solvent is adopted, prepares the mixed solution of hyperbranched poly triazole；
(2) detected material is detected using the mixed solution of hyperbranched poly triazole, observes system change in fluorescence, judge to be detected
Whether thing contains diarylamines age resistor.
The concentration of hyperbranched poly triazole described in step (1) is 10-6M～10-4M, mixed solvent is described in step (1)
The mixed liquor of the mixed liquor of the mixed liquor of water and tetrahydrofuran, water and acetone, methyl alcohol and tetrahydrofuran, ethanol and dichloromethane
The mixed liquor or methyl alcohol of the mixed liquor of mixed liquor, methyl alcohol and chloroform, methyl alcohol and DMF and dimethyl sulfoxide (DMSO)
Mixed liquor.
The water is 7/3～99/1 with the volume ratio of tetrahydrofuran, and the volume ratio of water and acetone is 7/3～99/1, methyl alcohol
It is 7/3～99/1 with the volume ratio of tetrahydrofuran, the volume ratio of ethanol and dichloromethane is 7/3～99/1, methyl alcohol and chloroform
Volume ratio is 7/3～99/1, and the volume ratio of methyl alcohol and DMF is 7/3～99/1, methyl alcohol and dimethyl sulfoxide (DMSO)
Volume ratio be 7/3～99/1.
Detected material described in step (2) needs to add in organic solvent before being detected.The organic solvent is tetrahydrochysene furan
One or more of mutter, acetone, dichloromethane, chloroform, toluene, chlorobenzene, DMF, dimethyl sulfoxide (DMSO).
Judge whether detected material has diarylamines age resistor to specifically refer to work as under fluorescence intensity described in step (2)
Drop, then contain diarylamines age resistor in detected material；Preferably, degree >=65% is declined.
Concentration of the detected material in system described in step (2) is 10-8M～10-4M。
The present invention has the following advantages and beneficial effect relative to prior art：
1st, the hyperbranched poly triazole that the present invention is utilized is obtained by cycloaddition polymerisation, and raw material is cheap and easy to get, and reaction need not
Catalyst, is carried out under air conditionses, and is had and solvent-free can be reacted；Reaction yield is very high, and post processing is simple, without the need for any multiple
Miscellaneous purge process, it is easy, it is easy to get；
2nd, hyperbranched poly triazole of the invention is used as fluorescence chemical sensor, when diarylamines age resistor is detected, with
Existing determination method is compared, and is pre-processed without the need for complicated detected material, such as Freezing smashing, is extracted repeatedly, concentration purification etc.
Process, detection sensitivity is high and selective good, inexpensive with portable, and quickly, accurate advantage can be used in real time, on the spot, high
It is selective, high sensitivity analysis.
Description of the drawings
Fig. 1 is hyperbranched poly triazole hb-P1 of the embodiment of the present invention 1 to the highly sensitive of diarylamines antioxidant compound 1
Property detection fluorescence spectra；In the case of wherein (a) exists for the antioxidant compound 1 of variable concentrations, hyperbranched poly triazole
Fluorescence intensity change curve map；B () is that the fluorescence intensity of hyperbranched poly triazole is different from addition when not adding antioxidant compound 1
Fluorescence intensity changes in contrast figure during the antioxidant compound 1 of content；
Fig. 2 be hyperbranched poly triazole hb-P1 of the embodiment of the present invention 1 to diarylamines antioxidant compound (1) and other
The block diagram of the fluorescence intensity contrast of aminated compounds (2～10)；
Fig. 3 is hyperbranched poly triazole hb-P1 of the embodiment of the present invention 1 to industrial conventional diarylamines age resistor chemical combination
Thing (1,11～14) and other common product of rubber and plastic additive (15～21) fluorescent quenching block diagrams；
Fig. 4 is the thermogravimetric curve figure of hyperbranched poly triazole hb-P1 of the embodiment of the present invention 1.
Specific embodiment
With reference to embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited
In this.Agents useful for same can routinely be buied if no special instructions from market in embodiment.
Embodiment 1
A kind of hyperbranched poly triazole, its structural formula is as shown in hb-P1：
Hyperbranched poly triazole hb-P1 has excellent heat endurance (thermogravimetric curve is shown in Fig. 4), and it is anti-to diarylamines old
The high sensitivity detection of agent, by taking antioxidant compound 1 as an example：
Detecting step：
The antioxidant compound 1 of different quality is dissolved in good solvent such as tetrahydrofuran, is subsequently adding the water of polytriazoles
With the tetrahydrofuran (volume ratio 9 of water and tetrahydrofuran:1) it is different so that the content of antioxidant compound 1 is obtained in mixed solution
Polytriazoles solution (concentration of antioxidant compound 1 be 0.5 μM, 1 μM, 2 μM, 4 μM, 6 μM, 8 μM, 10 μM, 12 μM, 20 μM, 30 μ
M, 40 μM, 50 μM), and test its fluorescence spectrum.As a result show, test limit can as little as 54nM, when the concentration of antioxidant compound 1
Only 10-5During M, you can the fluorescence of quenching hyperbranched poly triazole more than 90%.Before and after antioxidant compound 1 is added, fluorescence intensity
Change is big, and easily naked eyes are recognized.Concrete outcome is shown in Fig. 1.Fig. 1 is hyperbranched poly triazole hb-P1 of the embodiment of the present invention 1 to diaryl
The fluorescence spectra of the high sensitivity detection of amines antioxidants compound 1；Wherein (a) is the antioxidant compound 1 of variable concentrations
In the case of presence, the fluorescence intensity change curve map of hyperbranched poly triazole；B () is hyperbranched during antioxidant compound 1 not add
The fluorescence intensity of polytriazoles and the fluorescence intensity changes in contrast figure during antioxidant compound 1 for adding different content.
Embodiment 2
The hyperbranched poly triazole of the present invention shows high selectivity response to diarylamines age resistor, and control compounds are
The amine substances such as aromatic primary amine (2-3), fragrant tertiary amine (4-5), fatty amine (6-10)：
Detecting step：
The concentration of configuration compound 1-10 is 10-3The tetrahydrofuran solution of M, is then respectively adding the water of hyperbranched poly triazole
With the tetrahydrofuran (volume ratio 9 of water and tetrahydrofuran:1) in mixed solution, so that compound 1-10 concentration is obtained as 5 × 10-5M
Hyperbranched poly triazole solution, and test its fluorescence spectrum.As a result show, the fluorescence of hyperbranched poly triazole is only by age resistor chemical combination
Thing 1 is effectively quenched, and the fluorescence intensity contrast ratio before and after addition is close 20 times；And other amine substances are to hyperbranched poly triazole
Fluorescence intensity have little to no effect or only minimal effect.Test result illustrates that the hyperbranched poly triazole of the present invention can be selected
Selecting property only has response to diarylamines age resistor, and this is conducive to excluding in actual applications other amine substances to detection
Affect.Concrete outcome is shown in Fig. 2.Fig. 2 is hyperbranched poly triazole hb-P1 of the embodiment of the present invention 1 to diarylamines age resistor chemical combination
The block diagram of the fluorescence intensity contrast of thing (1) and other aminated compounds (2～10).
Embodiment 3
High selectivity inspection of the hyperbranched poly triazole of the present invention to industrial conventional diarylamines age resistor (11-14)
Survey, control compounds are the age resistor (15-17) of other common types in product of rubber and plastic, and other common additives such as increase
Modeling agent (18), fire retardant (19), lubricant (20), heat stabilizer (21)：
Detecting step：
Configuration compound 1, the concentration of 11-21 is 10-3The tetrahydrofuran solution of M, be then respectively adding polytriazoles water and
In the mixed solution of tetrahydrofuran, so that compound 1 is obtained, 11-21 concentration is 5 × 10-5The polytriazoles solution of M, and it is glimmering to test its
Light spectrum.As a result show, the fluorescence of hyperbranched poly triazole is only by diarylamines age resistor 1, and 11-14 compounds are effectively sudden
Go out, fluorescence intensity is quenched percentage more than 80%；And other kinds of age resistor, such as phenol antiager, ketone amines antioxidants,
Thiourea age resistor (15-17) etc., only has minimal effect to the fluorescence intensity of hyperbranched poly triazole.Meanwhile, in product of rubber and plastic its
(18-21) such as his common additive, such as plasticizer, fire retardant, lubricant, heat stabilizers is to the fluorescence of hyperbranched poly triazole
Without quenching effect.Test result illustrates that the hyperbranched poly triazole of the present invention can be selective only fragrant to two in complex environment
Base amines antioxidants has response, this considerably increases the reliability in actually detected application, and eliminates present analysis side
The complicated detected material preprocessing process that method needs, in real time, detect on the spot it is with the obvious advantage.Concrete outcome is shown in Fig. 3.Fig. 3 is
Hyperbranched poly triazole hb-P1 of the embodiment of the present invention 1 is to industrial conventional diarylamines antioxidant compound (1,11～14)
Product of rubber and plastic additive (15～21) the fluorescent quenching block diagram common with other.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention not by above-described embodiment
Limit, other any Spirit Essences without departing from the present invention and the change, modification, replacement made under principle, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (10)
1. application of a kind of hyperbranched poly triazole in detection diarylamines age resistor, it is characterised in that：The hyperbranched poly
Triazole has the structure shown in formula (I)：
In formula (I), R1, R3For identical or different organic group, R2To connect functional group, FxFluorine to be connected on phenyl ring is former
Son, x represents the number of F atom, and x is 2～4 integer；Wherein, R1, R3One kind in following chemical structural formula 1～18；R2
Any one in following structural formula 19～22；
Wherein, * represents the position of substitution.
2. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 1, it is characterised in that：
Specifically include following steps：
(1) mixed solvent is adopted, prepares the mixed solution of hyperbranched poly triazole；
(2) detected material is detected using the mixed solution of hyperbranched poly triazole, observes system change in fluorescence, judge that detected material is
It is no containing diarylamines age resistor.
3. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 2, it is characterised in that：
Mixed solvent described in step (1) is the mixed liquor of the mixed liquor of water and tetrahydrofuran, water and acetone, methyl alcohol and tetrahydrofuran
The mixing of the mixed liquor of the mixed liquor of mixed liquor, ethanol and dichloromethane, methyl alcohol and chloroform, methyl alcohol and DMF
The mixed liquor of liquid or methyl alcohol and dimethyl sulfoxide (DMSO).
4. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 3, it is characterised in that：
The volume ratio of the water and tetrahydrofuran is 7/3～99/1, and the volume ratio of water and acetone is 7/3～99/1, methyl alcohol and tetrahydrochysene furan
The volume ratio muttered is 7/3～99/1, and the volume ratio of ethanol and dichloromethane is 7/3～99/1, and the volume ratio of methyl alcohol and chloroform is
7/3～99/1, the volume ratio of methyl alcohol and DMF is 7/3～99/1, the volume ratio of methyl alcohol and dimethyl sulfoxide (DMSO)
For 7/3～99/1.
5. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 2, it is characterised in that：
The concentration of hyperbranched poly triazole described in step (1) is 10-6M～10-4M。
6. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 2, it is characterised in that：
Detected material described in step (2) needs to add in organic solvent before being detected.
7. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 6, it is characterised in that：
The organic solvent is tetrahydrofuran, and acetone, dichloromethane, chloroform, toluene, chlorobenzene, DMF, dimethyl is sub-
One or more of sulfone.
8. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 2, it is characterised in that：
Judge whether detected material has diarylamines age resistor to specifically refer to when fluorescence intensity declines described in step (2), then it is tested
Survey in thing and contain diarylamines age resistor.
9. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 8, it is characterised in that：
The fluorescence intensity declines degree >=65%, then contain diarylamines age resistor in detected material.
10. application of the hyperbranched poly triazole in detection diarylamines age resistor according to claim 2, its feature exists
In：Concentration of the detected material in system described in step (2) is 10-8M～10-4M。
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| US20080103273A1 (en) * | 2006-09-06 | 2008-05-01 | The Hong Kong University Of Science And Technology | Polytriazoles constructed by 1, 3-dipolar cycloaddition |
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| CN102585220A (en) * | 2012-01-16 | 2012-07-18 | 浙江大学 | Hyperbranched polytriazole formate as well as preparation method and application thereof |
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| CN105906807A (en) * | 2016-06-16 | 2016-08-31 | 华南理工大学 | Polytriazole with intrinsic flame retardance and preparing method and application thereof |
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2016
- 2016-09-14 CN CN201610824859.3A patent/CN106632102B/en active Active
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| US20080103273A1 (en) * | 2006-09-06 | 2008-05-01 | The Hong Kong University Of Science And Technology | Polytriazoles constructed by 1, 3-dipolar cycloaddition |
| CN102153748A (en) * | 2010-12-07 | 2011-08-17 | 浙江大学 | Hyperbranched polytriazole with aggregation induced light-emitting performance and preparation method and application of hyperbranched polytriazole |
| CN102585220A (en) * | 2012-01-16 | 2012-07-18 | 浙江大学 | Hyperbranched polytriazole formate as well as preparation method and application thereof |
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