CN109824614A - A kind of reactive ultraviolet absorber of the base containing benzotriazole and its preparation method and application - Google Patents
A kind of reactive ultraviolet absorber of the base containing benzotriazole and its preparation method and application Download PDFInfo
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Abstract
The applicant provides a kind of reactive ultraviolet absorber and preparation method thereof of base containing benzotriazole, and the ultraviolet absorber is the compound of structure shown in formula (I), and structure is the combination of benzotriazole base and carbon-carbon double bond.The method of the present invention raw material is cheap and easy to get, each raffinate stream yield is higher, the reactive ultraviolet absorber of the base containing benzotriazole synthesized by the method can improve the shortcomings that its surface migration and volatilization, it is relatively good with polymer-polymer miscibility, toxicity is low, and the fabric of dacron is since good characteristic is using more and more extensive, so the textile with excellent uvioresistant performance can be prepared.
Description
Technical field
The present invention relates to textile finishing technical fields, ultraviolet more particularly, to a kind of reactivity containing benzotriazole base
Absorbent and preparation method thereof and the application of the UV absorption monomer in Polyester Textiles anti UV finishing.
Background technique
Since twentieth century, along with the rapid development of industry, the problem of environmental pollution, becomes increasingly conspicuous, refrigerant, foaming
The use of the modern science and technology product such as agent causes the compounds such as a large amount of freon to be trapped in atmosphere, can occur one with ozone
Serial chain reaction, stronger to the damage capability of ozone layer and ozone concentration reduce, and will lead to more short wavelength ultraviolets
It is irradiated to ground, is adversely affected to the mankind.
Various countries worldwide and area have a set of requirement and standard of oneself to the colour fasteness to sunlight of textile material.
Long-term ultraviolet light irradiation, can make fabric turn yellow, the uvioresistant ability for how improving fabric just seems particularly significant.Terylene is
An important species in synthetic fibers has application in many fields such as weaving and industrial product.And the fabric of polyester fabric,
Under conditions of long-term direct sunlight, the aging of material can be aggravated, reduce the service life of fabric, excessively by ultraviolet radioactive,
It can cause a variety of skin lesions.The basic component of terylene is polyethylene terephthalate, in addition to two in molecule
It holds and does not contain polar group outside the presence of alcoholic extract hydroxyl group, hydrophily is poor, so, research ultraviolet absorber changes the grafting of terylene
Property has very important meaning.
Common ultraviolet absorber mainly has salicylic acid esters, triazines, benzophenone, benzotriazole etc..Wherein,
The ultraviolet absorber absorption coefficient of salicylic acid esters is low, and molecule easily resets dihydroxy benaophenonel and its derivative in pairs；Triazines
Ultraviolet absorber have coloring, some visible light can be absorbed；The ultraviolet absorber of benzophenone there is also photostability compared with
Difference, also yellowing and the more expensive defect of price；Benzotriazole ultraviolet absorber is a kind of important light stabilizer, phase
Than for benzophenone, its absorbing wavelength range is wider, thus absorbancy index is higher between wavelength 300-385nm,
Close to the requirement of desirable absorption agent, and it to visible light substantially without absorption.
The mechanism of action of benzotriazole ultraviolet absorber uvioresistant is based on tautomer structure, benzotriazole molecule
On the atom different there are two kinds of cloud densities of nitrogen-atoms and oxygen atom, under the influence of ultraviolet irradiation, phenol chemical combination
Object (existence form before extinction) is mutually converted with its tautomer, and the phenol structure in ground state is more stable.But benzene
And polar hydroxyl is contained only in the molecular structure of the ultraviolet absorber of triazole type, and negligible amounts, it is not easy securely to arrange to knitting
On object, and molecular weight is smaller, and migration volatilization is easy to happen during arrangement, results in finishing effect decline in this way, resists
UV resistance decline.
In consideration of it, a kind of easy reactive ultraviolet absorber arranged to the base containing benzotriazole on fabric is developed, and
With excellent uvioresistant performance, the uvioresistant function textile of good anti-aging property, have a very important significance.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, this application provides a kind of ultraviolet suctions of reactivity of base containing benzotriazole
Receive agent and its preparation method and application.The method of the present invention raw material is cheap and easy to get, each raffinate stream yield is higher, is synthesized by the method
The base containing benzotriazole reactive ultraviolet absorber can improve its surface migration and volatilization the shortcomings that and polymer-polymer miscibility
Relatively good, toxicity is low, and the fabric of dacron is since good characteristic is using more and more extensive, so can prepare with excellent
The textile of different uvioresistant performance.
Technical scheme is as follows:
The applicant provides a kind of reactive ultraviolet absorber of base containing benzotriazole, and the ultraviolet absorber is formula
(I) compound of structure shown in:
The applicant additionally provides the preparation method of the reactive ultraviolet absorber, the specific steps are as follows:
(1) ortho-nitraniline 4.14g and water 50mL is mixed, the HCl that concentration is 36.0~38.0wt% is added
8.6mL is cooled to -4~4 DEG C, and the concentration that 0.032mol is added is the NaNO of 30wt%2Aqueous solution reacts 20-40min；
(2) add urea or sulfamic acid to decompose excessive nitrous acid, stir 5-15min, until starch-KI test paper is in micro- blue,
Filtering, obtains clarification pale yellow solution；
(3) solution temperature -5~5 DEG C are kept, resorcinol 5.00g, dehydrated alcohol 100 are added dropwise while stirring
The mixed solution of mL and water 90mL, react 2~3h, and filtering is recrystallized with dehydrated alcohol and water V:V=1:1；
(4) the sodium hydroxide solution 100mL that dehydrated alcohol 100mL is added in above-mentioned product 7.80g and concentration is 16wt% is taken,
Stirring, is heated to flowing back, is rapidly added reducing agent thiourea dioxide, so that reactant becomes rufous from atropurpureus, then instead
Liquid is answered to become clear light yellow, the reaction was continued 50-60min；
(5) insoluble matter is filtered out, filtrate is neutralized to pH for 2-3, until in solution with HCl solution while stirring in ice bath
There is pale yellow precipitate precipitation, filter, is recrystallized with dehydrated alcohol and water V:V=1:1, obtain product 2 benzotriazole base -5- hydroxyl
Base phenol；
(6) by above-mentioned product 2 benzotriazole base -5- hydroxyl phenol 11.35g in 7.0mL triethylamine and 40mL tetrahydrofuran
Middle stirring and dissolving；The mixed solution of acryloyl chloride 9.05g and 20mL tetrahydrofuran is added dropwise while stirring into reaction solution, referring to thin
Layer chromatography, used solvent are ethyl acetate/petroleum ether/methylene chloride, and ice bath reacts 8-9h；
(7) then by mix products saturation NaHCO3It is washed in solution, takes upper layer rufous oily solution in flask
In be evaporated；Vacuum drying is washed with ethanol solution, obtains product 2- (2 '-hydroxyls -4 '-acryloyl group)-benzotriazole.
Preferably, step (6) 2 benzotriazole base -5- hydroxyl phenol and the molar ratio of triethylamine and acryloyl chloride are
1:1:2.Preferably, used solvent volume ratio is ethyl acetate: petroleum ether: methylene chloride=(1.8~2): (4.6~
5.2):1。
Preferably, the temperature of step (1), (2), (3) diazo coupling and step (6) substitution reaction is set in ice bath item
Under part, the temperature of step (4) reduction reaction is set in 65-80 DEG C.
The applicant additionally provides the reactive ultraviolet absorber and is preparing the application in anti-ultraviolet material, specific side
Method are as follows:
It is 10~12% that the UV absorption monomer of formula (I) described structure and solution, which are hybridly prepared into mass percentage concentration,
Finishing fluid, bath raio 1:26~32, by dacron second dipping and rolling in the above solution, first under the conditions of 60~75 DEG C preliminary drying 3~
8min, after bake 2~5min under the conditions of 120~140 DEG C, sufficiently washed with acetone soln, drying to constant weight, be made uvioresistant
Polyester material.
Preferably, the solution is n,N-Dimethylformamide, that is, DMF.
Preferably, the pick-up of the padding process is 100%.
The present invention is beneficial to be had the technical effect that
The raw material of the reactive ultraviolet absorber of present invention base containing benzotriazole is relatively common, greatly reduces and is produced into
This；Three step synthetic products of the method for the present invention point, the yield that product is made in each process are higher.Technique for applying is made through the invention
Ultraviolet ray resistant textiles have excellent uvioresistant performance, uvioresistant is high-efficient, and UPF value is risen to by the 45 of former terylene
223.74。
Detailed description of the invention
Fig. 1 is reaction principle schematic diagram of the present invention.
Specific embodiment
Reaction principle and embodiment shown in 1 with reference to the accompanying drawing, is specifically described the present invention.
One, reactive ultraviolet absorber of the base containing benzotriazole and preparation method thereof embodiment
Embodiment 1:
Ortho-nitraniline 4.14g and water 50mL are added in 250mL three-necked flask and stirred, w36.0~38.0% is added
HCl 8.6mL, be cooled to 0 DEG C, the NaNO of w=0.30 be added2Aqueous solution reacts 40min, urea or sulfamic acid is added to decompose
The nitrous acid of amount stirs 15min, until starch-KI test paper is in micro- blue, filtering obtains clarification pale yellow solution, pours into 500mL tri-
It in mouth flask, is kept for 5 DEG C of solution temperature, the mixed of resorcinol 5.00g, dehydrated alcohol 100mL and water 90mL is added while stirring
Solution is closed, 2h is reacted, filtering obtains red azo product 6.06g, yield 77.93% with alcohol-water (V:V=1:1) recrystallization；
The red azo product of 7.80g is taken, the sodium hydroxide solution 100mL of dehydrated alcohol 100mL, w=0.16 are added to
In the three-necked flask of 500mL, stirring, temperature is stablized at 80 DEG C, is heated to flowing back, is rapidly added reducing agent thiourea dioxide, makes
Reactant from atropurpureus becomes rufous, then reaction solution becomes clear light yellow, the reaction was continued 60min, filters out insoluble
Object, filtrate are neutralized to pH=2-3 while stirring in ice bath with HCl solution, it can be observed that there is pale yellow precipitate analysis in solution
Out, it filters, obtains product 2 benzotriazole base -5- hydroxyl phenol, with alcohol-water (V:V=1:1) recrystallization, obtain white needles crystalline substance
Body 3.67g, yield 53.90% (opposite azo compound meter)；
The triethylamine of 11.35g2- benzotriazole base -5- hydroxyl phenol and 7.0mL is put into 250mL three-necked flask and is stirred
It mixes, the acryloyl chloride and 20mL tetrahydrofuran of 7.24g is added dropwise when the rear tetrahydrofuran that 40mL is added dissolves .5 DEG C into reaction solution
Mixed solution, the speed 1mL/min of dropwise addition is controlled, referring to thin-layered chromatography, solvent: ethyl acetate/petroleum of 2:5:1
Ether/methylene chloride, ice bath react 9h, then by mix products saturation NaHCO3It is washed in solution, takes upper layer rufous oily
Shape solution is evaporated in flask and washs vacuum drying with ethanol solution, obtains 7.51g light yellow crystal, yield 53.44%.
Embodiment 2:
Ortho-nitraniline 4.14g and water 50mL are added in 250mL three-necked flask and stirred, addition w=36.0~
38.0% HCl 8.6mL, is cooled to 0 DEG C, and the NaNO of w=0.30 is added2Aqueous solution reacts 30min, adds urea or sulfamic acid
Excessive nitrous acid is decomposed, 10min is stirred, until starch-KI test paper is in micro- blue, filtering obtains clarification pale yellow solution, pours into
It in 500mL three-necked flask, is kept for 0 DEG C of solution temperature, resorcinol 5.00g, dehydrated alcohol 100mL and water is added dropwise while stirring
2h is reacted in the mixed solution of 90mL, stirring, and filtering obtains red azo product with alcohol-water (V:V=1:1) recrystallization
6.74g, yield 86.67%；
The red azo product of 7.80g is taken, the sodium hydroxide solution 100mL of dehydrated alcohol 100mL, w=0.16 are added to
In the three-necked flask of 500mL, stirring, temperature is stablized at 70 DEG C, is heated to flowing back, is rapidly added reducing agent thiourea dioxide, makes
Reactant from atropurpureus becomes rufous, then reaction solution becomes clear light yellow, the reaction was continued 50min, filters out insoluble
Object, filtrate are neutralized to pH=2-3 while stirring in ice bath with HCl solution, it can be observed that there is pale yellow precipitate analysis in solution
Out, it filters, obtains product 2 benzotriazole base -5- hydroxyl phenol, with alcohol-water (V:V=1:1) recrystallization, obtain white needles crystalline substance
Body 3.84g, yield 56.40% (opposite azo compound meter)；
The triethylamine of 11.35g2- benzotriazole base -5- hydroxyl phenol and 7.0mL is put into 250mL three-necked flask and is stirred
It mixes, the acryloyl chloride and 20mL of 9.05g is added dropwise in the rear tetrahydrofuran that 40mL is added while stirring into reaction solution when dissolving .0 DEG C
The mixed solution of tetrahydrofuran, referring to thin-layered chromatography, solvent: ethyl acetate/petroleum ether/methylene chloride of 2:5:1, ice bath
React 8h, then by mix products saturation NaHCO3It is washed in solution, upper layer rufous oily solution is taken to steam in flask
Dry washs vacuum drying with ethanol solution, obtains 7.80g light yellow crystal, yield 55.51%.
Two, the reactive ultraviolet absorber Application Example of the base containing benzotriazole
Application Example 1:
It is 10% that the reactive ultraviolet absorber of the base containing benzotriazole synthesized by embodiment 1, which is configured to mass percent,
Finishing fluid, dacron to be processed first with acetone soln washing and drying and is weighed into weight, grafted monomers are in room temperature condition
Under, it is dissolved with n,N-Dimethylformamide (DMF) solution, bath raio 1:30, second dipping and rolling, pick-up 100%, second dipping and rolling, first
Preliminary drying 5min under the conditions of 70 DEG C, after bake 3min under the conditions of 120 DEG C, sufficiently washed with acetone soln, drying to constant weight, system
Obtain uvioresistant dacron.Measuring UPF value is 202.15.
Application Example 2:
It is 12% that the reactive ultraviolet absorber of the base containing benzotriazole synthesized by embodiment 1, which is configured to mass percent,
Finishing fluid, dacron to be processed first with acetone soln washing and drying and is weighed into weight, grafted monomers are in room temperature condition
Under, it is dissolved with n,N-Dimethylformamide (DMF) solution, bath raio 1:30, second dipping and rolling, pick-up 100%, second dipping and rolling, first
Preliminary drying 5min under the conditions of 70 DEG C, after bake 3min under the conditions of 130 DEG C, sufficiently washed with acetone soln, drying to constant weight, system
Obtain uvioresistant dacron.Measuring UPF value is 223.74.
Application Example 3:
It is 14% that the reactive ultraviolet absorber of the base containing benzotriazole synthesized by embodiment 1, which is configured to mass percent,
Finishing fluid, dacron to be processed first with acetone soln washing and drying and is weighed into weight, grafted monomers are in room temperature condition
Under, it is dissolved with n,N-Dimethylformamide (DMF) solution, bath raio 1:30, second dipping and rolling, pick-up 100%, second dipping and rolling, first
Preliminary drying 5min under the conditions of 70 DEG C, after bake 3min under the conditions of 140 DEG C, sufficiently washed with acetone soln, drying to constant weight, system
Obtain uvioresistant dacron.Measuring UPF value is 236.28.
Comparative example 1:
The reactive ultraviolet absorber of certain commercially available base containing benzotriazole is prepared according to the method for Application Example 2 whole
Uvioresistant dacron after reason.Measuring UPF value is 189.74.
Comparative example 2:
The reactive ultraviolet absorber of certain commercially available base containing benzotriazole is prepared according to the method for Application Example 2 whole
Uvioresistant dacron after reason.Measuring UPF value is 192.62.
Three, performance test
1, the measurement of ultimate strength and elongation:
The measurement of the ultimate strength and elongation of reference standard GB/T3923-1997 fabric is tested former with strength tester
Each 3 pieces through broadwise of the dacron that dacron, modification are crossed, it is uniformly cut into the rectangle for being about 15cm, width about 6cm,
It pulls trimming yarn and makes 5cm, test result is referring to table 1.
Table 1
The test data of table 1 shows more former dacron, the dacron that modification is crossed through being lost to ultimate strength
About 1%, broadwise ultimate strength loss about 2%, after ultraviolet light for 24 hours, former dacron through to ultimate strength
Loss about 14% or so, broadwise ultimate strength loss about 22%, after ultraviolet light for 24 hours, what modification was crossed is washed
Synthetic fibre fabric through to ultimate strength loss about 10%, broadwise ultimate strength loss about 18%, this explanation is by modification
Dacron has certain uvioresistant performance.And the fabric of modification is little through broadwise strength loss, it is seen that Ci Zhonggong
Skill has no effect on the normal use of fabric.
2, the surface migration test of anti ultraviolet agent
The uvioresistant terylene that Application Example 2, comparative example 1, comparative example 2 are prepared is placed in dry and ventilated city
It is interior, it prevents ultraviolet light from irradiating, tests its UPF numerical value after a predetermined time, the results are shown in Table 2.
Table 2
| Standing time | Application Example 2 | Comparative example 1 | Comparative example 2 |
| 10 days | 219.35 | 182.03 | 188.81 |
| 30 days | 213.94 | 175.95 | 180.95 |
| 60 days | 206.23 | 168.41 | 171.23 |
3, the surface volatility test of anti ultraviolet agent
The uvioresistant terylene that Application Example 2, comparative example 1, comparative example 2 are prepared carries out ultraviolet light irradiation [temperature
(60 ± 3) DEG C, 0.89W/m2], its UPF numerical value is tested after a predetermined time, and the results are shown in Table 3.
Table 3
| Irradiation time | Application Example 2 | Comparative example 1 | Comparative example 2 |
| 24 hours | 198.37 | 159.62 | 163.34 |
| 100 hours | 175.51 | 134.28 | 135.63 |
| 150 hours | 160.92 | 114.78 | 118.12 |
Claims (8)
1. a kind of reactive ultraviolet absorber of base containing benzotriazole, it is characterised in that the ultraviolet absorber is shown in formula (I)
The compound of structure:
2. the preparation method of reactivity ultraviolet absorber described in claim 1, it is characterised in that specific step is as follows:
(1) ortho-nitraniline 4.14g and water 50mL is mixed, the HCl 8.6mL that concentration is 36.0~38.0wt% is added
- 4~4 DEG C are cooled to, the concentration that 0.032mol is added is the NaNO of 30wt%2Aqueous solution reacts 20-40min；
(2) add urea or sulfamic acid to decompose excessive nitrous acid, stir 5-15min, until starch-KI test paper is in micro- blue, filter,
Pale yellow solution must be clarified；
(3) solution temperature -5~5 DEG C are kept, resorcinol 5.00g, dehydrated alcohol 100mL and water 90mL are added dropwise while stirring
Mixed solution, reacts 2~3h, and filtering is recrystallized with dehydrated alcohol and water V:V=1:1；
(4) the sodium hydroxide solution 100mL that dehydrated alcohol 100mL is added in above-mentioned product 7.80g and concentration is 16wt% is taken, is stirred
It mixes, is heated to flowing back, be rapidly added reducing agent thiourea dioxide, so that reactant becomes rufous from atropurpureus, then react
Liquid becomes clear light yellow, the reaction was continued 50-60min；
(5) insoluble matter is filtered out, filtrate is neutralized to pH with HCl solution while stirring in ice bath as 2-3, light until having in solution
Yellow mercury oxide is precipitated, and filtering is recrystallized with dehydrated alcohol and water V:V=1:1, obtains product 2 benzotriazole base -5- hydroxy benzenes
Phenol；
(6) above-mentioned product 2 benzotriazole base -5- hydroxyl phenol 11.35g is stirred in 7.0mL triethylamine and 40mL tetrahydrofuran
Mix dissolution；The mixed solution of acryloyl chloride 9.05g and 20mL tetrahydrofuran is added dropwise while stirring into reaction solution, referring to thin layer color
Spectrometry, used solvent are ethyl acetate/petroleum ether/methylene chloride, and ice bath reacts 8-9h；
(7) then by mix products saturation NaHCO3It is washed in solution, upper layer rufous oily solution is taken to steam in flask
It is dry；Vacuum drying is washed with ethanol solution, obtains product 2- (2 '-hydroxyls -4 '-acryloyl group)-benzotriazole.
3. preparation method according to claim 2, it is characterised in that: step (6) 2 benzotriazole base -5- hydroxy benzenes
The molar ratio of phenol and triethylamine and acryloyl chloride is 1:1:2.
4. preparation method according to claim 2, it is characterised in that: used solvent volume ratio is ethyl acetate:
Petroleum ether: methylene chloride=(1.8~2): (4.6~5.2): 1.
5. preparation method according to claim 2, it is characterised in that: step (1), (2), (3) diazo coupling and step
Suddenly the temperature of (6) substitution reaction is set under condition of ice bath, and the temperature of step (4) reduction reaction is set in 65-80 DEG C.
6. reactivity ultraviolet absorber of any of claims 1 or 2 is preparing the application in anti-ultraviolet material, it is characterised in that:
The UV absorption monomer of formula (I) described structure and solution are hybridly prepared into the arrangement that mass percentage concentration is 10~12%
Liquid, bath raio 1:26~32, by dacron second dipping and rolling in the above solution, first 3~8min of preliminary drying under the conditions of 60~75 DEG C,
2~5min is baked under the conditions of 120~140 DEG C afterwards, is sufficiently washed with acetone soln, drying to constant weight, and uvioresistant terylene is made
Material.
7. application according to claim 6, it is characterised in that: the solution is n,N-Dimethylformamide, that is, DMF.
8. application according to claim 6, it is characterised in that: the pick-up of the padding process is 100%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117986663A (en) * | 2023-12-26 | 2024-05-07 | 上海焦能新材料有限公司 | High-temperature-resistant corrosion-resistant alloy rubber and preparation method thereof |
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