A kind of Hinered phenols antioxidant and its synthetic method
Technical field
The present invention relates to a kind of synthetic method of antioxidant, relate more particularly to a kind of Hinered phenols antioxidant and its synthesis
Method, belong to antioxidant and organic chemical synthesis technical field.
Background technology
Hinered phenols antioxygen has that antioxidant effect is good, and heat endurance is high, pollution-free to product, not colored, and with product phase
The advantages that capacitive is good, turn into a kind of most primary antioxidant of polymeric material field application.
So far, methods have been developed many kinds of Hinered phenols antioxidants, wherein high polymer material hindered phenol
Kind antioxidant mainly have Switzerland Ciba-Geigy research and develop Irganox1076 (II), Irganox1010 (III),
Irganox1098 (IV) and antioxidant 3114 (V) (wherein t-Bu is the tert-butyl group, similarly hereinafter), the structural formula of these antioxidant is as follows:
However, the melting temperature of these Hinered phenols antioxidants is relatively low, the wherein best antioxidant of heat endurance (V), its
Melting range is 218.0-225.5 DEG C, and heat-resistant stability and resistance to extractable are poor, is only used for processing and the relatively low high score of use condition
In sub- material product.In addition, industrial antioxidant (V) is for raw material with 2,6- DI-tert-butylphenol compounds, paraformaldehyde and cyanuric acid,
Hexamethylenetetramine is catalyst, and first alcohol and water is solvent, the isothermal reaction 6 hours under the conditions of 689.4KPa, 135 DEG C and obtain
Arrive.The technological reaction condition is harsh, and production cost is higher.
With widening for high polymer material application field, such as it is used as the high polymer material of high artesian pipe and On The Oil And Gas Transportation pipe
PE100+, its processing temperature are 220-240 DEG C, and original Hinered phenols antioxidant is difficult to meet to require, this requires that exploitation is new
The high temperature resistant antioxidant of type.
In the early 1960s, the Hinered phenols antioxidant 1330 that Shell Co. Ltd of the U.S. is developed using mesitylene as bridging base
(VI) there is good heat endurance (240-243 DEG C of melting range) and processing stability, can be widely applied to polyolefin (PP, PE
Deng), polyamide, phenolic resin, nylon, material, its structural formula such as rubber it is as follows:
Because the antioxidant has good performance, people have carried out substantial amounts of further investigation to its synthetic method, and it is closed
Mainly include benzylalcohol method, benzyl oxide method, benzyl ester method, one pot reaction method etc. into method, such as:
Berris et al. 3,5- di-t-butyl -4- hydroxyl benzyl methyl ethers and mesitylene are raw material, and catalyst is methanesulfonic acid, oneself
Alkane makees solvent, and back flow reaction is carried out at 78 DEG C, reacts reaction mixture alkaline wash, filtering, vacuum after terminating
Dry, obtain the antioxidant 1330, its yield is 74%, and the fusing point of product is 240-243 DEG C.
Mina et al. is raw material using 3,5- di-t-butyl -4- hydroxyl benzyl methyl ethers and mesitylene, and sulfuric acid and acetic acid mix
Catalyst is closed, dichloromethane makees solvent, and reactant is cooled into 5 DEG C by ice bath, reacted 3-4 hours, it is remaining that reaction terminates removal
Sulfuric acid, reaction mixture wash with appropriate alkaline sodium carbonate or sodium bicarbonate solution, finally recrystallizes, filter, drying, into
Work(is prepared for antioxidant 1330.The yield of antioxidant 1330 synthesized using the method is higher, and product colour is shallower, and impurity is few, and
Easy to operate, caused discarded object is less, is easy to industrialized production.
Although as described above, disclose the good antioxidant of multiple performance in the prior art, for it is new, have more
Good resistant to elevated temperatures antioxidant and its synthetic method, still suffer from the necessity for continuing research, and this is also current Hinered phenols antioxidant neck
Study hotspot and emphasis in domain, are even more where the power that the present invention is accomplished and basis is leaned on.
The content of the invention
In order to obtain having more preferable resistant to elevated temperatures novel antioxidant and its synthetic method, present inventor has performed substantial amounts of depth
Enter research, after substantial amounts of creative work has been paid, so as to complete the present invention.
Specifically, the present invention relates to following aspects.
One side, the present invention relates to the Hinered phenols antioxidant shown in a kind of formula (I):
Found by test, formula (I) hindered phenol antioxygen has very excellent melting range, and its melting range is up to 254.6-
255.1 DEG C (so as to have excellent high temperature resistant property);Moreover, add the PE100+ special material for tube HDPE4806 of the antioxidant
Oxidation induction period be 84.25 minutes, be significantly higher than the PE100+ special material for tube HDPE4806's that with the addition of antioxidant 1330
Oxidation induction period (70.55 minutes), this proves that it has excellent antioxygenic property.
Second aspect, it is described the present invention relates to a kind of synthetic method of high temperature resistant Hinered phenols antioxidant of the formula (I)
Method includes:In the presence of solid supported base catalyst, lower formula (II) compound is with lower formula (III) compound in organic solvent
In reacted, reaction it is post-treated, so as to obtain the formula (I) compound,
In the synthetic method of formula of the present invention (I) high temperature resistant Hinered phenols antioxidant, the solid supported alkalescence is urged
Agent is prepared in accordance with the following steps:
S1:The apatite powder that granularity is 30-40 μm is added in strong alkali aqueous solution, is sufficiently stirred 40-50 minutes, so
Deionized water is fully washed afterwards, until eluate is neutrality, and is fully dried, obtains alkali process apatite powder;By the alkali
Processing apatite powder calcines 55-65 minutes at 400-500 DEG C, then naturally cools to room temperature, and is fully ground, and obtains grain
Spend the processing apatite powder for 10-20 μm;
S2:The wet chemical that molar concentration is 1-2mol/L is prepared, the processing apatite powder is soaked in institute
State in wet chemical, and the microwave treatment 60-70 minutes under microwave power 600W, then filter, by gained solid sequentially
Respectively washed 2-3 times with absolute ethyl alcohol, deionized water, vacuum drying is complete, most after being calcined at 450 ± 20 DEG C 55-65 minutes, certainly
So cooling, obtains the first dipping powder;
S3:The cesium fluoride aqueous solution that molar concentration is 0.4-0.8mol/L is prepared, using equi-volume impregnating by described the
One dipping powder infusion is in the cesium fluoride aqueous solution, until the carbon loaded in final gained solid supported base catalyst
The mol ratio of sour potassium and cesium fluoride is preferably 1: 0.2-0.4, and most preferably 1: 0.3;After the completion of dipping, filtering, gained solid is used
Deionized water is fully washed 2-3 times, most complete after being dried in vacuo at 120-140 DEG C, produces the solid supported base catalysis
Agent.
Wherein, in the step S1, the strong alkaline aqueous solution is the NaOH aqueous solution or the KOH aqueous solution, the strong basicity
The molar concentration of the aqueous solution is 3-4mol/L, such as can be 3mol/L, 3.5mol/L or 4mol/L.
Wherein, in the step S1, the mass ratio of the apatite powder and the strong alkali aqueous solution is 1: 4-5, example
Such as can be 1: 4,1: 4.5 or 1: 5.
Wherein, in the step S1, the alkali process apatite powder is calcined into 55-65 minutes at 400-500 DEG C,
Such as calcination processing can be carried out in Muffle furnace, calcining heat is 400-500 DEG C, such as can be 400 DEG C, 450 DEG C or 500 DEG C;
Calcination time is 55-65 minutes, such as can be 55 minutes, 60 minutes or 65 minutes.
Wherein, in the step S2, the molar concentration of the wet chemical is 1-2mol/L, such as can be
1mol/L, 1.5mol/L or 2mol/L.
Wherein, in the step S2, the microwave treatment can be carried out in microwave generating apparatus, such as can be in micro-wave oven
Or carried out in microwave generator, those skilled in the art can carry out suitably selecting and determining, no longer be described in detail herein.
Wherein, in the step S2, the processing apatite powder in terms of quality gram (g) with volume milliliter (ml)
The ratio of the wet chemical of meter be 1: 3.5-5, such as can be 1: 3.5,1: 4,1: 4.5 or 1: 5, also will every 1 gram (g) institute
Processing apatite powder is stated to be soaked in 3.5-5 milliliters (ml) wet chemical.
Wherein, in the step S3, the molar concentration for preparing the cesium fluoride aqueous solution is 0.4-0.8mol/L, such as can
For 0.4mol/L, 0.6mol/L or 0.8mol/L.
Wherein, in the step S3, by method of the described first dipping powder infusion in the cesium fluoride aqueous solution
For equi-volume impregnating, this method is the very known and conventional technology in dipping field, and those skilled in the art can
Use this method with having no any technical difficulty, be no longer described in detail herein.
Wherein, in the step S3, inventor has found, potassium carbonate and fluorination in final solid supported base catalyst
It is that arbitrary proportion can obtain best technique effect that the ratio of caesium, which is not, but there is a specific preferred scope.More
Specifically, can be with when the potassium carbonate in final solid supported base catalyst and the mol ratio of cesium fluoride are 1: 0.2-0.4
Extraordinary effect, most preferably 1: 0.3 are obtained, now both can play concerted catalysis effect the most excellent.
Therefore, the suitable incipient impregnation time may be selected, to cause the carbonic acid in final solid supported base catalyst
The mol ratio of potassium and cesium fluoride is fallen into above-mentioned restriction scope, and this is the conventional capability that those skilled in the art should possess,
This is no longer described in detail.
In the synthetic method of formula of the present invention (I) high temperature resistant Hinered phenols antioxidant, formula (II) compound with
The mol ratio of formula (III) compound is 3-6: 1, such as can be 3: 1,4: 1,5: 1 or 6: 1.
In the synthetic method of formula of the present invention (I) high temperature resistant Hinered phenols antioxidant, formula (II) compound with
The mass ratio of the solid supported base catalyst is 1: 0.1-0.2, such as can be 1: 0.1,1: 0.15 or 1: 0.2.
In the synthetic method of formula of the present invention (I) high temperature resistant Hinered phenols antioxidant, the organic solvent is benzene, first
Benzene or dimethylbenzene.The dosage of the organic solvent does not have strict restriction, and those skilled in the art can be carried out according to actual conditions
It is suitable to select no longer to be retouched in detail herein to facilitate reaction to carry out and post-process with determination, such as its dosage size
State.
In the synthetic method of formula of the present invention (I) high temperature resistant Hinered phenols antioxidant, reaction temperature is 60-80 DEG C,
Such as it can be 60 DEG C, 70 DEG C or 80 DEG C.
In the synthetic method of formula of the present invention (I) high temperature resistant Hinered phenols antioxidant, the reaction time is that 15-35 is small
When, such as can be 15 hours, 20 hours, 25 hours, 30 hours or 35 hours.
In the synthetic method of formula of the present invention (I) high temperature resistant Hinered phenols antioxidant, reaction terminate after it is described after
Handle and be:After reaction terminates, negative pressure filtration, is cooled to 2-5 DEG C by filtrate, separates out solid, filter out solid again, successively while hot
Washed 3-4 times respectively with benzene, deionized water, gained solid is finally dried in vacuo 10-15 hours at 70-90 DEG C, that is, obtained
Formula (I) the high temperature resistant Hinered phenols antioxidant.
As described above, the invention provides a kind of new high temperature resistant Hinered phenols antioxidant and its synthetic method, it is described
Compound has excellent resistance to elevated temperatures and an antioxygenic property, and the synthetic method by unique reactant, specific urge
Use of agent etc., purpose product is obtained so as to high yield, brand-new synthetic method is provided for the compound, had good
Good application prospect, promotional value and actual production potentiality.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of the gained high temperature resistant Hinered phenols antioxidant of embodiment 1.
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of the gained high temperature resistant Hinered phenols antioxidant of embodiment 1.
Fig. 3 is the mass spectrogram of the gained high temperature resistant Hinered phenols antioxidant of embodiment 1.
Embodiment
Below by specific embodiment, the present invention is described in detail, but the purposes of these exemplary embodiments and
Purpose is only used for enumerating the present invention, not forms any type of any restriction to the real protection scope of the present invention, more non-to incite somebody to action
Protection scope of the present invention is confined to this.
Preparation example 1:The preparation of solid supported base catalyst
S1:By the apatite powder that granularity is 30-40 μm be added to for 4.5 times of its quality strong alkali aqueous solution (for mole
The concentration 3.5mol/L NaOH aqueous solution) in, it is sufficiently stirred 45 minutes, then deionized water is fully washed, until eluate is
Neutrality, and fully dry, obtain alkali process apatite powder;By the alkali process apatite powder in Muffle furnace in 450 DEG C
Lower calcining 60 minutes, then naturally cools to room temperature, and is fully ground, and obtains the processing apatite powder that granularity is 10-20 μm;
S2:The wet chemical that molar concentration is 1.5mol/L is prepared, the processing apatite powder is soaked in institute
(the processing apatite powder in terms of quality gram (g) and the potassium carbonate in terms of volume milliliter (ml) are stated in wet chemical
The ratio of the aqueous solution is 1: 4.25), and microwave treatment 65 minutes under microwave power 600W, then filter, by gained solid sequentially
Respectively washed 3 times with absolute ethyl alcohol, deionized water, vacuum drying is complete, most after being calcined 60 minutes at 450 DEG C, natural cooling, obtains
To the first dipping powder;
S3:The cesium fluoride aqueous solution that molar concentration is 0.6mol/L is prepared, is soaked using equi-volume impregnating by described first
Stain powder infusion is in the cesium fluoride aqueous solution, until the potassium carbonate loaded in final gained solid supported base catalyst
Mol ratio with cesium fluoride is 1: 0.3;After the completion of dipping, filtering, gained solid fully washs 3 times with deionized water, most after
It is dried in vacuo completely at 130 DEG C, produces the solid supported base catalyst, be named as C1.
Contrast preparation example 1-2:Alkali process and the investigation of calcining
(distinguish unused strong alkali aqueous solution in addition to the processing of the strong alkali aqueous solution in step S1, calcination operation is not carried out respectively
Carry out not carrying out calcination processing after alkali process, alkali process), other operation all sames, so as to which preparation example 1 be repeated,
Sequentially obtain contrasting preparation example 1 and 2, gained solid supported base catalyst is named as D1, D2 successively.
Contrast preparation example 3-4:Load the investigation of component
Contrast preparation example 3:(the processing apatite powder that step S1 is obtained directly is walked in addition to step S2 is dispensed
Rapid S3 incipient impregnation, the load capacity of cesium fluoride are still the actual negative carrying capacity in preparation example 1), other operations are constant, so as to
Preparation example 1 is repeated, gained solid supported base catalyst is named as in D3, namely the catalyst without load potassium carbonate.
Contrast preparation example 4:(only proceeding to step S2) in addition to step S3 is dispensed, other operations are constant, so as to
Preparation example 1 is repeated, gained solid supported base catalyst (namely first dipping powder in step S2) is named as D4,
Without load cesium fluoride i.e. in the catalyst.
Contrast preparation example 5-10:Load component molar than investigation
Except by the potassium carbonate in final solid supported base catalyst and the mol ratio of cesium fluoride by 1 in preparation example 1:
0.3 is varied to outside other ratios in table 1, and other operations are constant, so as to which preparation example 1 be repeated, obtains contrast and prepares
Example 5-10, both mol ratios and final gained catalyst name see the table below 1.
The investigation of the potassium carbonate of table 1. and cesium fluoride load mol ratio
Below, reaction synthesis formula (I) compound is carried out to formula (II) compound and formula (III) compound to investigate, from
And influence of the different catalysts for end reaction result is investigated.
Embodiment 1
Into appropriate organic solvent-benzene, formula (II) compound β-(3,5- di-t-butyl -4- hydroxyls described in 450mmol are added
Phenyl) propionic acid, 100mmol formulas (III) compound p-phenylenediamine and solid supported base catalyst C1 (formula (II) compounds
Mass ratio with the solid supported base catalyst is 1: 0.15), then controlling reaction temperature is 70 DEG C, and at such a temperature
Stirring reaction 25 hours;After reaction terminates, negative pressure filtration, is cooled to 2-5 DEG C by filtrate, separates out solid, filter out again while hot
Solid, successively washed respectively 3 times with benzene, deionized water, finally gained solid is dried in vacuo 12.5 hours at 80 DEG C, obtained
Formula (I) the high temperature resistant Hinered phenols antioxidant, yield 97.6%.
Fusing point:254.6-255.1℃;
From accompanying drawing 1:Wave number is 3641cm-1Locate be for the characteristic absorption peak of free phenolic hydroxyl group (- OH), wave number
3290cm-1Locate as the characteristic absorption peak of N-H in association phenolic hydroxyl group and amido link, wave number 1652cm-1Locate as C=O in amido link
Characteristic absorption peak.
From accompanying drawing 2, it is the tert-butyl group-C (CH at 1.30-1.45 that chemical shift, which is,3)3In Hydrogen Proton, 2.42-2.63
Locate as the α-CH that are connected in β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid antioxidant groups with phenyl ring2- in Hydrogen Proton,
It is β-the CH that are connected in β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid antioxidant groups with phenyl ring at 2.81-2.972- in
Hydrogen Proton, at 5.08 be Hydrogen Proton in phenolic hydroxyl group, at 6.95-7.12 be Hydrogen Proton in p-phenylenediamine bridging base on phenyl ring,
It is Hydrogen Proton in amide groups (- CONH-) at 7.42, at 7.30-7.42 is β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid
Hydrogen Proton in antioxidant groups on phenyl ring.
From accompanying drawing 3, occurs the quasi-molecular ion peak [M+] of the antioxidant at 629.49.
Embodiment 2
Into appropriate organic solvent toluene, formula (II) compound β-(3,5- di-t-butyl -4- hydroxyls described in 300mmol are added
Base phenyl) propionic acid, 100mmol formulas (III) compound p-phenylenediamine and solid supported base catalyst C1 (formula (II) chemical combination
The mass ratio of thing and the solid supported base catalyst is 1: 0.2), then controlling reaction temperature is 60 DEG C, and in the temperature
Lower stirring reaction 35 hours;After reaction terminates, negative pressure filtration, is cooled to 2-5 DEG C by filtrate, separates out solid, filter again while hot
Go out solid, successively washed respectively 4 times with benzene, deionized water, finally gained solid is dried in vacuo 10 hours at 90 DEG C, obtained
Formula (I) the high temperature resistant Hinered phenols antioxidant, yield 97.1%.
Its fusing point, infrared data, nucleus magnetic hydrogen spectrum data and mass spectrometric data are the same as embodiment 1.
Embodiment 3
Into appropriate organic solvent dimethylbenzene, formula (II) compound β-(3,5- di-t-butyl -4- described in 600mmol are added
Hydroxy phenyl) (formula (II) is changed by propionic acid, 100mmol formulas (III) compound p-phenylenediamine and solid supported base catalyst C1
The mass ratio of compound and the solid supported base catalyst is 1: 0.1), then controlling reaction temperature is 80 DEG C, and in the temperature
The lower stirring reaction of degree 15 hours;After reaction terminates, negative pressure filtration, is cooled to 2-5 DEG C by filtrate, separates out solid, again mistake while hot
Filter out solid, successively with benzene wash 3 times, deionized water wash 4 times, it is small that gained solid is finally dried in vacuo to 15 at 70 DEG C
When, obtain the formula (I) high temperature resistant Hinered phenols antioxidant, yield 97.5%.
Its fusing point, infrared data, nucleus magnetic hydrogen spectrum data and mass spectrometric data are the same as embodiment 1.
Comparative example 1-6:The influence of alkali process and calcining to catalytic effect
Comparative example 1-3:In addition to the catalyst C1 in embodiment 1-3 is replaced with into D1 respectively, other operations are constant, so as to
Embodiment 1-3 is repeated, sequentially obtains comparative example 1-3.
Comparative example 4-6:In addition to the catalyst C1 in embodiment 1-3 is replaced with into D2 respectively, other operations are constant, so as to
Embodiment 1-3 is repeated, sequentially obtains comparative example 4-6.
As a result 2 are see the table below, compares for convenience and lists embodiment 1-3 products collection efficiency in the lump.
Table 2
Wherein, the order of the yield of product and each embodiment/comparative example corresponds, for example, for embodiment 1-3 and
Speech, the products collection efficiency of 97.6% corresponding embodiment 1, the products collection efficiency of 97.1% corresponding embodiment 2, and 97.5% corresponding embodiment
3 products collection efficiency.Other similar expression in the table 2 and below each table also have identical corresponding relation, no longer go to live in the household of one's in-laws on getting married one by one
State.
As can be seen here:1st, when apatite does not carry out highly basic processing, products collection efficiency is caused to be significantly reduced (see comparative example
1-3);2 and when apatite not highly basic processing after do not carry out calcination processing when, yield reduce it is the most notable.This should be highly basic
Processing and calcination processing eliminate impurity therein, improve the regularity and uniformity of apatite internal gutter, so as to favourable
In follow-up active ingredient adsorption and uniformly attachment.
Comparative example 7-12:Load influence of the component to catalytic effect
Comparative example 7-9:In addition to the catalyst C1 in embodiment 1-3 is replaced with into D3 respectively, other operations are constant, so as to
Embodiment 1-3 is repeated, sequentially obtains comparative example 7-9.
Comparative example 10-12:In addition to the catalyst C1 in embodiment 1-3 is replaced with into D4 respectively, other operations are constant, from
And embodiment 1-3 is repeated, sequentially obtain comparative example 10-12.
As a result 3 are see the table below, compares for convenience and lists embodiment 1-3 products collection efficiency in the lump.
Table 3
As can be seen here:1st, when only loading cesium fluoride or only loading potassium carbonate, all yield will be caused to have significant drop
It is low;But yield when only loading cesium fluoride will more be less than yield when only loading potassium carbonate, this proves individually load carbonic acid
The effect of potassium is better than cesium fluoride.2nd, it was unexpectedly determined that when loading potassium carbonate and cesium fluoride simultaneously, products collection efficiency has aobvious
What is write improves, and this proves that both components have played the concerted catalysis effect of uniqueness, and this is surprising.
Comparative example 13-18:Load the influence that component molar compares catalytic effect
In order to investigate the influence of active component potassium carbonate and cesium fluoride mol ratio to end reaction result, thereby using difference
Catalyst and repeat implement products collection efficiency highest embodiment 1, also i.e. the catalyst C1 in embodiment 1 is replaced with successively
D5, D6, D7, D8, D9 and D10, other operations are constant, as a result see the table below 4, compare for convenience and by the product of embodiment 1
Yield is listed in the lump.
Table 4
As can be seen here:1st, the load mol ratio of potassium carbonate and cesium fluoride can significantly affect products collection efficiency, when for 1: 0.3 when
Best effect can be obtained.And when being below or above the ratio, it will all cause products collection efficiency to have even notable to a certain degree
Reduction.This should be when such ratio, can play best catalyzing cooperation activity;2nd, on the basis of 1: 0.3, even
Identical deviation value, effect when higher than 1: 0.3 be better than less than 1: 0.3 effect (such as comparative example 17 and 18 is for 1:
0.3 has identical deviation value, but the effect of comparative example 17 is better than comparative example 18).
Test case:The measure of oxidation induction period
The length of oxidation induction period may indicate that the quality of the oxidation resistance of antioxidant, in the present invention, oxidation induction
The method of testing of phase is specific as follows:
At ambient temperature, it is using GH-10DC types high-speed mixer that 0.5g antioxidant and 500g PE100+ tubing is special
Material HDPE4806 is sufficiently mixed;The sample mixed is extruded on SHJ-92 double screw extruders, wire drawing and is granulated, extrusion temperature
Spend for 200 ± 0.1 DEG C;Then, at room temperature by granular samples after air drying 48 hours, in Tetrahedron2022
100cm × 100cm × 0.5cm thin slice is depressed on type hydraulic machine in 180 ± 0.1 DEG C of conditions, by sample thin slice be cut into 1cm ×
1cm × 0.5cm size;Sample is put into crucible, then sample that crucible is positioned over to differential scanning calorimeter device is supported
On frame, under the conditions of nitrogen (flow velocity 50mL/min) with 20 DEG C/min of speed by room temperature temperature programming to 200 ± 0.1 DEG C,
After constant temperature 3 minutes, then gas switched into same nitrogen flow rate identical oxygen, gas switching point is designated as testing starting point, by temperature
Degree is held constant at 200 ± 0.1 DEG C, after there is heat release point, continues constant temperature 2 minutes, is finally cooled to room temperature.From experiment starting point
The time needed to heat release point is the oxidation induction period of sample.
Wherein, when the antioxidant added in above-mentioned method of testing is respectively the formula (I) compound, the antioxidant of the present invention
During 1330 (VI) (antioxidant 1330 that Shell Co. Ltd of the U.S. researches and develops i.e. in " background technology "), by test, respective oxygen
Change induction period see the table below 5, list respective melting range (resistance to elevated temperatures) in the lump.
Table 5
As can be seen here, formula (I) compound resistance to elevated temperatures of the present invention will be significantly better than antioxidant 1330 (VI), and
Its oxidation resistance is also significantly better than antioxidant 1330 (VI), so as in exotic material or material that processing temperature is higher
Had a good application prospect in preparation and potentiality.
In summary, it is described anti-the invention provides a kind of novel fire resistant Hinered phenols antioxidant and its synthetic method
Oxygen agent has excellent resistance to elevated temperatures and antioxygenic property, and the synthetic method passes through unique reactant, specific catalysis
Use of agent etc., purpose product is obtained so as to high yield, brand-new synthetic method is provided for the compound, had good
Application prospect, promotional value and actual production potentiality.
It should be appreciated that the purposes of these embodiments is merely to illustrate the present invention and is not intended to the protection model of the limitation present invention
Enclose.In addition, it should also be understood that, after the technology contents of the present invention have been read, those skilled in the art can make each to the present invention
Kind change, modification and/or variation, all these equivalent form of values equally fall within the guarantor that the application appended claims are limited
Within the scope of shield.