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, belongs to antioxidant and organic chemical synthesis technical field.
Background technology
Hinered phenols antioxygen has antioxidant effect good, and heat endurance is high, pollution-free to product, not colored, and with product phase
The advantages of capacitive is good, as 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 obtained
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 is 220-240 DEG C, and original Hinered phenols antioxidant is difficult to meet to require, this requires exploitation 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. develops using mesitylene as bridging base
(VI) there is good heat endurance (240-243 DEG C of melting range) and processing stability, polyolefin (PP, PE is can be widely applied to
Deng), polyamide, phenolic resin, nylon, the material such as rubber, its structural formula 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, for example:
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%, the fusing point of product is 240-243 DEG C.
Mina et al. uses 3,5- di-t-butyl -4- hydroxyl benzyl methyl ethers and mesitylene to be raw material, and sulfuric acid and acetic acid are mixed
Catalyst is closed, dichloromethane makees solvent, reactant is cooled to 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 recrystallization, suction filtration, 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, the discarded object of generation is less, it is easy to industrialized production.
As described above, although disclose the good antioxidant of multiple performance in the prior art, but for it is new, with more
Good resistant to elevated temperatures antioxidant and its synthetic method, still suffer from the necessity for continuing to study, 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, its melting range is up to 254.6-
255.1 DEG C (so that with excellent high temperature resistant property);Moreover, adding 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
It is middle to be reacted, react post-treated, so that the formula (I) compound is obtained,
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:Granularity is added in strong alkali aqueous solution for 30-40 μm of apatite powder, 40-50 minutes are sufficiently stirred for, so
Deionized water is fully washed afterwards, until eluate is neutrality, and is fully dried, obtains alkali process apatite powder;By the alkali
Apatite powder is handled in being calcined 55-65 minutes at 400-500 DEG C, room temperature is then naturally cooled to, and is fully ground, grain is obtained
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 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 55-65 minutes at 450 ± 20 DEG C, 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, for example, 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, by the alkali process apatite powder in calcining 55-65 minutes at 400-500 DEG C,
Calcination processing can be for example carried out in Muffle furnace, calcining heat is 400-500 DEG C, for example, can be 400 DEG C, 450 DEG C or 500 DEG C;
Calcination time is 55-65 minutes, for example, 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, for example, 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, for example 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, for example 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 the wet chemical of 3.5-5 milliliters (ml).
Wherein, in the step S3, the molar concentration for preparing the cesium fluoride aqueous solution is 0.4-0.8mol/L, for example may be used
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
The ratio of caesium is not that arbitrary proportion can obtain best technique effect, but there is a specific preferred scope.More
Specifically, can be with when the potassium carbonate and the mol ratio of cesium fluoride in final solid supported base catalyst are 1: 0.2-0.4
Obtain extraordinary effect, most preferably 1: 0.3, 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, for example, 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, for example, 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 consumption of the organic solvent does not have strict restriction, and those skilled in the art can be carried out according to actual conditions
Suitable selection is with determining, such as its consumption size is no longer retouched in detail herein with facilitating reaction to carry out and post-process
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,
It for example 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, for example 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
It is processed as:After reaction terminates, negative pressure filtration, 2-5 DEG C is cooled to by filtrate while hot, is separated out solid, solid is filtered out again, successively
Washed 3-4 times respectively with benzene, deionized water, finally gained solid is 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, with 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 only be used for enumerate the present invention, not to the present invention real protection scope constitute it is any type of it is any limit, it is more non-will
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 for 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 with absolute ethyl alcohol, deionized water 3 times, vacuum drying is complete, most after being calcined 60 minutes at 450 DEG C, natural cooling is obtained
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 alkali process, alkali process and do not carry out calcination processing after finishing), other operation all sames, so that preparation example 1 is 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 is still the actual negative carrying capacity in preparation example 1), other operations are constant, so that
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 proceed to step S2) in addition to step S3 is dispensed, other operations are constant, so that
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 and the mol ratio of cesium fluoride in final solid supported base catalyst by 1 in preparation example 1:
0.3 is varied to outside other ratios in table 1, and other operations are constant, so that preparation example 1 is repeated, obtains contrast and prepares
Example 5-10, both mol ratios and final gained catalyst name see the table below 1.
The potassium carbonate of table 1. and cesium fluoride load the investigation of mol ratio
Below, reaction synthesis formula (I) compound is carried out to formula (II) compound and formula (III) compound to investigate, from
And investigated influence of the different catalysts for end reaction result.
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, 2-5 DEG C is cooled to by filtrate while hot, is separated out solid, is filtered out again
Solid, is successively washed 3 times, finally gained solid is dried in vacuo 12.5 hours at 80 DEG C, is obtained respectively with benzene, deionized water
Formula (I) the high temperature resistant Hinered phenols antioxidant, yield is 97.6%.
Fusing point:254.6-255.1℃;
From accompanying drawing 1:Wave number is 3641cm-1Locate as the characteristic absorption peak of free phenolic hydroxyl group (- OH), wave number is
3290cm-1Locate for association phenolic hydroxyl group and amido link in N-H characteristic absorption peak, wave number is 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 the β-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, be Hydrogen Proton in phenolic hydroxyl group at 5.08, at 6.95-7.12 be p-phenylenediamine bridging base in Hydrogen Proton 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, the quasi-molecular ion peak [M+] of the antioxidant is occurred in that 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, 2-5 DEG C is cooled to by filtrate while hot, is separated out solid, is filtered again
Go out solid, successively washed respectively with benzene, deionized water 4 times, finally gained solid is dried in vacuo 10 hours at 90 DEG C, obtained
Formula (I) the high temperature resistant Hinered phenols antioxidant, yield is 97.1%.
Its fusing point, infrared data, nucleus magnetic hydrogen spectrum data and mass spectrometric data be the same as Example 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, 2-5 DEG C is cooled to by filtrate while hot, separates out solid, again mistake
Filter out solid, successively washed with benzene 3 times, deionized water wash 4 times, gained solid is finally dried in vacuo to 15 at 70 DEG C small
When, the formula (I) high temperature resistant Hinered phenols antioxidant is obtained, yield is 97.5%.
Its fusing point, infrared data, nucleus magnetic hydrogen spectrum data and mass spectrometric data be the same as Example 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 that
Embodiment 1-3 is repeated, comparative example 1-3 is sequentially obtained.
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 that
Embodiment 1-3 is repeated, comparative example 4-6 is sequentially obtained.
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 yield of product and the order of each embodiment/comparative example are corresponded, such as embodiment 1-3
Speech, the products collection efficiency of 97.6% correspondence embodiment 1, the products collection efficiency of 97.1% correspondence 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 reduction it is the most notable.This should be highly basic
Processing and calcination processing eliminate impurity therein, the regularity and uniformity of apatite internal gutter are improved, so that favorably
In follow-up active ingredient adsorption and uniform 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 that
Embodiment 1-3 is repeated, comparative example 7-9 is sequentially obtained.
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 yield when only loading cesium fluoride more will be less than only load 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, will all cause products collection efficiency to have even notable to a certain degree
Reduction.This should, 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 (for example 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 granulated, extrusion temperature
Spend for 200 ± 0.1 DEG C;Then, at room temperature by granular samples in 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, the sample that crucible then is positioned over into differential scanning calorimeter device is supported
On frame, under the conditions of nitrogen (flow velocity is 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, occurs after 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, and respective melting range (resistance to elevated temperatures) is listed 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 that 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, with 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 limitation protection model of the invention
Enclose.In addition, it will also be appreciated that after the technology contents of the present invention have been read, those skilled in the art can make each to the present invention
Change, modification and/or variation are planted, all these equivalent form of values equally fall within the guarantor that the application appended claims are limited
Within the scope of shield.