CN1109478A - Application method for improved compound alkylphenol esters oxidation preventive - Google Patents

Application method for improved compound alkylphenol esters oxidation preventive Download PDF

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CN1109478A
CN1109478A CN 94119406 CN94119406A CN1109478A CN 1109478 A CN1109478 A CN 1109478A CN 94119406 CN94119406 CN 94119406 CN 94119406 A CN94119406 A CN 94119406A CN 1109478 A CN1109478 A CN 1109478A
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hydroxyl
butyl
propionic acid
ester
pentaerythritol ester
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CN1047394C (en
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李扬
王德充
洪定一
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Beijing Research Institute of Beijing Yanshan Petrochemical Corp
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Beijing Research Institute of Beijing Yanshan Petrochemical Corp
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Abstract

The modified anti-oxidant is a mixture of tetra 3-(3,5-di-tertiary butyl-4-hydroxyl) propionic acid] pentaerythritol ester and p-3-(3,5-di-tertiary butyl-4-hydroxyl) propionic acid octodecester, their proportions are 1:3.5-3.5:1. It can be used in rubber material, thermoplastic elastic material, plastics, synthetic fiber and organic oil substnces, it can double the induction period of oxidant.

Description

Application method for improved compound alkylphenol esters oxidation preventive
The present invention relates to rubber thermoplastic elastic body material, plastic material, synthon and oil product type organic matter and use the improvement of oxidation inhibitor method, particularly the improvement of polybutadiene rubber, polyisoprene rubber, vinylbenzene and alkadiene multipolymer, polyolefin plastics material, alkane, aromatic hydrocarbons thermal oil goods application oxidation inhibitor method.
Oxidation inhibitor is a kind of important fine chemical product, is used widely in the synthetic materials field.At present, be to improve the employed oxidation inhibitor of over-all properties of rubber-plastics material, synthon and oil product type organic matter, by single type to compound development.The complex type antioxidant kind is more, and most popular is alkyl phenolic ester class and phosphorous acid esters compound binary or ternary antioxidant systems.
Polymer Engineering and Science, 1980,20, [10] talk about [3-(3 in, 5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester and 2,6 di tert butyl 4 methyl phenol respectively with 3-2,4-di-tert-butyl-phenyl) phosphorous acid ester compound binary stablizer (anti-aging agent).USP3,285,855(1966,11,15) provide with containing alkyl, hydroxyl, the ester of phenyl makes the organic materials method of stabilizing, also mentioning can be other oxidation inhibitor, antiozonidate, thermo-stabilizer, UV light absorber, coloring material, dyestuff, pigment, metal-chelate mixture etc., use among the prescription and method of its invention, comprise and use oxidation inhibitor four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester, but specifically do not provide oxidation inhibitor four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) the preferred composite methods of propionic acid octadecyl ester, more there are not best mixing match scope and antioxidant effect.
Along with the widespread use of science and technology development and rubber-plastics material, more and more higher to the requirement of its antioxidant property.Therefore, select the best complex application method of oxidation inhibitor, become major issue anxious to be solved in rubber-plastics material, the material production of oil product class, storing, the application process.Particularly make toughner, when producing high impact resistance polystyrene, require elastomeric material to have extremely low gel content with low cis 1 rubber.And use single type oxidation inhibitor or other complex type antioxidant, all be difficult to achieve the goal.
Purpose of the present invention, be to address the above problem, a kind of application method of improved compound hindered phenolic ester kind antioxidant is provided, further improve the antioxidant property of elastomeric material, thermoplastic elastic material, plastics, synthon and oil product type organic matter, particularly improve the antioxidant property of elastomeric material, make it have extremely low gel content.
The invention provides a kind of application method of improved compound hindered phenolic ester kind antioxidant.The technical scheme of this method is oxidation inhibitor four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) the propionic acid octadecyl ester mixes, four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the weight ratio scope of propionic acid octadecyl ester was generally 1: 3.5~3.5: 1.
Four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the preferable weight ratio scope of propionic acid octadecyl ester is 1: 2.8~2.8: 1.
Four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester optimum weight ratio scope is 1: 2~2: 1.
Above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of elastomeric material, thermoplastic elastic material, plastics, synthon and oil product type organic matter.
Above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of polybutadiene rubber, polyisoprene rubber, divinyl and styrol copolymer rubber and other various elastomeric materials.
Above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of the segmented copolymer (SIS) of the segmented copolymer (SBS) of vinylbenzene and divinyl and vinylbenzene and isoprene.
Above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) mixing match of propionic acid octadecyl ester is applied to the anti-oxidation method of plastic materials such as polyethylene, polypropylene, polystyrene.
Above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of alkane, aromatic hydrocarbons thermal oil goods.
In the anti-oxidation method of above-mentioned elastomeric material, thermoplastic elastic material, plastics, synthon and oil product organic substance, adopt four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) mixture of propionic acid octadecyl ester is made oxidation inhibitor, with four [3-(3,5-di-t-butyl-4-hydroxyl) weight ratio of propionic acid octadecyl ester is controlled in 1: 3.5~3.5: 1 scopes, and the antioxidant effect of system significantly improves; With four [3-(3,5-di-t-butyl-4-hydroxyl) weight ratio of propionic acid octadecyl ester is controlled in 1: 2.8~2.8: 1 scopes, and the antioxidant effect of system is more remarkable; [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3 with four, 5-di-t-butyl-4-hydroxyl) weight ratio of propionic acid octadecyl ester is controlled in 1: 2~2: 1 scopes, unexpectedly finds that the antioxidant effect of system strengthens exponentially.
The oxidation induction period of compound alkylphenol esters oxidation preventive of the present invention is significantly higher than four [3-(3 of single type, 5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester, also be significantly higher than four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) the propionic acid octadecyl ester respectively with other oxidation inhibitor compound binary or multi-component compound oxidation inhibitor mutually.
The improved compound alkylphenol esters oxidation preventive application method of the present invention can make be doubled and redoubled the oxidation period of oxidation inhibitor, demonstrates outstanding synergism.Like this, antioxidant system then has better antioxidant property, and makes elastomeric material have extremely low gel content, and painted shallow, texture is good.
Further specify the present invention below in conjunction with embodiment, but be not to limit the scope of the invention.
Embodiment 1
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 22.5 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 22.5 grams drop in the 2000 ml physiological saline bottles, add 150 milliliters of toluene, shake, make its whole dissolvings, add 1500 milliliters of hexanaphthenes again, it is stand-by to shake up the back.
Get monomer divinyl weight concentration and be 10%, transformation efficiency is 50 kilograms of 100% low cis 1 rubber glues, adds 1.65 liters of above-mentioned oxidation inhibitor solution, after mixing, obtains dried glue through the glue post-treating method of routine.The gel content of this glue is a 0.007%(weight).The oxidation induction period of oxidation inhibitor is 133 minutes.
Embodiment 2
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 10.2 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 34.8 grams.
All the other are with embodiment 1.
This glue gel content is 0.009%(weight).The oxidation induction period of oxidation inhibitor is 78 minutes.
Embodiment 3
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 15 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 30 grams.
Replace low cis 1 rubber glue with high-cis 1 rubber glue (the divinyl weight ratio is 10%, and transformation efficiency is 100%).
All the other are with embodiment 1.
The glue gel content is a 0.009%(weight).The oxidation induction period of oxidation inhibitor is 85 minutes.
Embodiment 4
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 20.1 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 24.9 grams.
Replace low cis 1 rubber glue with butadiene-styrene copolymer rubber solutions (monomer weight concentration is 10%, and transformation efficiency is 100%).
All the other are with embodiment 1.
Gel content is a 0.008%(weight in the glue).The oxidation induction period of oxidation inhibitor is 112 minutes.
Embodiment 5
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 24.9 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 20.1 grams.
Replace low cis 1,4 polybutadiene rubber glue with polyisoprene rubber glue (the isoprene weight concentration is 10%, and transformation efficiency is 100%).
All the other are with embodiment 1.
The gel content of this glue is a 0.008%(weight).The oxidation induction period of oxidation inhibitor is 105 minutes.
Embodiment 6
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 30 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 15 grams.
Segmented copolymer (SBS) solution (monomer weight concentration is 10%, and transformation efficiency is 100%) with vinylbenzene and divinyl replaces low cis 1 rubber glue.
All the other are with embodiment 1.
This thermoplastic elastomer gel content is a 0.009%(weight).The oxidation induction period of oxidation inhibitor is 93 minutes.
Embodiment 7
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 34.8 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 10.2 grams.
Segmented copolymer (SIS) solution (monomer weight concentration is 10%, and transformation efficiency is 100%) with vinylbenzene and isoprene replaces low cis 1 rubber glue.
All the other are with embodiment 1.
The gel content of this thermoplastic elastomer is a 0.009%(weight).
The oxidation induction period of oxidation inhibitor is 89 minutes.
Embodiment 8
(mix long carbochain saturated hydrocarbons oil at 500 kilograms of YD-132 thermal oils, Jiangyin, China Jiangsu chemical industry one factory's product) adds four [3-(3 in, 5-di-t-butyl-4-hydroxyl) propionic acid] 1.09 kilograms of pentaerythritol esters, add 3-(3 again, 5-di-t-butyl-4-hydroxyl) 1.71 kilograms of propionic acid octadecyl esters.Stirring makes its whole dissolvings.
This oil used 30 months under 310 ℃ of conditions continuously, and no coking phenomenon in the boiler tube, oil product do not have the rotten situation of thickness.
Embodiment 9
At 500 kilograms of YD-340 thermal oils (based on the BTX aromatics class oil of alkylnaphthalene, BeiJing, China research institute of Yanshan Petrochemical Co. product) adds 1.71 kilogram of four [3-(3 in, 5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester, add 1.09 kilograms of 3-(3 again, 5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester stirs and makes its dissolving.
This oil used 30 months under 320 ℃ of conditions continuously, and no coking phenomenon in the boiler tube, oil product do not have the rotten situation of thickness.
Embodiment 10
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 20.1 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 24.9 grams, directly add in 5 kilograms of polypropylene.
Embodiment 11
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 24.9 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 20.1 grams.Directly add in 5 kilograms of thing polyethylene.
Embodiment 12
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 22.5 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 22.5 grams, add in 5 kilograms of polystyrene.
Comparative Examples 1
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 45 grams.
All the other are with embodiment 1.
This glue, gel content are 0.030%(weight).
Oxidation inhibitor is that oxidation induction period is 62 minutes.
Comparative Examples 2
Take by weighing 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 45 grams.
All the other are with embodiment 1.
This glue gel content is 0.035%(weight).
The oxidation induction period of oxidation inhibitor is 33 minutes.
Comparative Examples 3
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 22.5 gram 3-(2, the 4-di-tert-butyl-phenyl) phosphorous acid ester 22.5 grams.
All the other are with embodiment 1.
This glue gel content is 0.020%(weight).
The oxidation induction period of oxidation inhibitor is 47 minutes.
Comparative Examples 4
Take by weighing 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 22.5 grams, 2,6 di tert butyl 4 methyl phenol 22.5 grams.
All the other are with embodiment 1.
This glue, gel, content are 0.030%(weight).
The oxidation induction period of oxidation inhibitor is 34 minutes.
Comparative Examples 5
Take by weighing four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester 8.2 grams, 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester 36.8 grams.
All the other are with embodiment 1.
This glue, gel, content are 0.015%(weight).
Be 70 minutes hydrogenation inductive phase of oxidation inhibitor.
Comparative Examples 6
2.34 kilograms of [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol esters that takes by weighing four, 3-(3,5-di-t-butyl-4-hydroxyl) 0.46 kilogram of propionic acid octadecyl ester.
All the other are with embodiment 8.
This thermal oil uses under 310 ℃ of conditions just must be changed in 18 months.
Comparative Examples 7
0.46 kilogram of [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester that takes by weighing four, 3-(3,5-di-t-butyl-4-hydroxyl) 2.34 kilograms of propionic acid octadecyl esters.
All the other are with embodiment 9.
This thermal oil used 18 months under 320 ℃ of conditions, just must change.
The oxidation induction period of oxidation inhibitor and gel content see Table 1 in embodiment, the Comparative Examples.
Table
Sequence number The oxidation inhibitor oxidation induction period (minute) Gel content (%) weight)
Embodiment 1 133 0.007
Embodiment 2 78 0.009
Embodiment 3 85 0.009
Embodiment 4 112 0.008
Embodiment 5 105 0.008
Embodiment 6 93 0.009
Embodiment 7 89 0.009
Embodiment 8 98
Embodiment 9 97
Embodiment 10 114
Embodiment 11 107
Comparative Examples 1 62 0.030
Comparative Examples 2 33 0.035
Comparative Examples 3 47 0.020
Comparative Examples 4 34 0.030
Comparative Examples 5 70 0.015
Comparative Examples 6 62
Comparative Examples 7 33
Annotate:
1. the mensuration of oxidation induction period:
The TG-DTA(Japan PTC-10A of company thermal-analysis instrumentation of science) logotype, constant heatingrate under nitrogen atmosphere reaches aerating oxygen (70cc/min) after the balance, DTA:100(+ μ V to 150 ℃), TG:100mg.Walk lower velocity: 2.5mm/min.
2. gel content determining:
Use 20 μ stainless (steel) wires to filter and measure (cat net method).
From embodiment, Comparative Examples and table 1 as can be seen, adopt oxidation inhibitor application method of the present invention, with oxidation inhibitor four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) control of the mixing match of propionic acid octadecyl ester just can be received ideal heat resistanceheat resistant, oxidation effectiveness within the scope of the present invention.The oxidation induction period of oxidation inhibitor is long, and the gel content of rubber elastomer class material is lower than 0.01%(weight) below, oil product class material life cycle rises appreciably.Otherwise, do not adopt oxidation inhibitor application method of the present invention, not with four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester mixing match mutually compound or two kinds of antioxygen components are controlled within the scope of the invention, then the oxidation induction period of oxidation inhibitor is short, the gel content height of rubber elastomer class material, and oil product class material life cycle is short.

Claims (15)

1, a kind of application method that makes the improved compound alkyl phenolic ester class anti-aging agent of organic substance stabilization, [3-(3 with four, 5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester and 3-(3,5-di-t-butyl-4-hydroxyl) two kinds of anti-aging agent of propionic acid octadecyl ester mix, [3-(3 to it is characterized in that four, 5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to [the weight ratio scope of 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester is 1: 3.5~3.5: 1.
2, according to the method for claim 1, [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester that it is characterized in that four is to 3-(3,5-di-t-butyl-4-hydroxyl) the preferable weight ratio scope of propionic acid octadecyl ester is 1: 2.8~2.8: 1.
3, according to the method for claim 1, [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester that it is characterized in that four is to 3-(3,5-di-t-butyl-4-hydroxyl) propionic acid octadecyl ester optimum weight ratio scope is 1: 2~2: 1.
4, according to the method for claim 1, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) mixing match of propionic acid octadecyl ester is applied to the anti-oxidation method of elastomeric material, thermoplastic elastic material, plastics, synthon and oil product type organic matter.
5, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of polybutadiene rubber.
6, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) mixing match of propionic acid octadecyl ester is applied to the anti-oxidation method of polyisoprene rubber.
7, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of butadiene-styrene copolymer rubber.
8, according to the method for right 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of vinylbenzene and butadiene block copolymer (SBS).
9, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) mixing match of propionic acid octadecyl ester is applied to the anti-oxidation method of vinylbenzene and isoprene block copolymer (SIS).
10, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of polypropylene material.
11, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of polythene material.
12, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of alkane thermal oil.
13, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of aromatic hydrocarbons thermal oil.
14, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of polyvinyl aromatic hydroxy compound.
15, according to the method for claim 1 and 4, it is characterized in that above-mentioned four [3-(3,5-di-t-butyl-4-hydroxyl) propionic acid] pentaerythritol ester is to 3-(3,5-di-t-butyl-4-hydroxyl) the mixing match range applications of propionic acid octadecyl ester is in the anti-oxidation method of polystyrene.
CN94119406A 1994-12-22 1994-12-22 Application method for improved compound alkylphenol esters oxidation preventive Expired - Lifetime CN1047394C (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1093551C (en) * 1998-09-01 2002-10-30 四川联合大学 High-density polyethylene based composition with high thermal conductivity

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JPS5874737A (en) * 1981-10-29 1983-05-06 Adeka Argus Chem Co Ltd Ethylene copolymer resin composition
JPS5896638A (en) * 1981-12-04 1983-06-08 Asahi Chem Ind Co Ltd Polymer composition
JPS6386039A (en) * 1986-09-30 1988-04-16 Toshiba Corp Display device for simulation result
JPH0299541A (en) * 1988-10-05 1990-04-11 Mitsui Toatsu Chem Inc Polypropylene resin composition
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1093551C (en) * 1998-09-01 2002-10-30 四川联合大学 High-density polyethylene based composition with high thermal conductivity

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