CN102942725A - Composition for providing thermal stability for polyolefin - Google Patents
Composition for providing thermal stability for polyolefin Download PDFInfo
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- CN102942725A CN102942725A CN2012104238912A CN201210423891A CN102942725A CN 102942725 A CN102942725 A CN 102942725A CN 2012104238912 A CN2012104238912 A CN 2012104238912A CN 201210423891 A CN201210423891 A CN 201210423891A CN 102942725 A CN102942725 A CN 102942725A
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- polyolefine
- composition
- dialkylamine
- thermostability
- mixture
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Abstract
The invention relates to a composition for providing thermal stability for polyolefin, characterized in that: the composition comprises a mixture of N,N-dialkyl hydramine and N,N-dialkyl amine, hindered phenol, phosphite and eleaostearic acid metal salt, and the weight ratio of the mixture to hindered phenol to phosphite to eleaostearic acid metal salt is 0.05-2:1:2-3:0.5-1, the N,N-dialkyl hydramine is represented by R1R2NH, N,N-dialkyl amine is represented by R1R2NOH, wherein R1 and R2 are C12-C30 alkyl, and are same or different.
Description
Technical field
The present invention relates to a kind of composition, relate to particularly a kind of composition that thermostability is provided for polyolefine.
Background technology
Polyolefine comprises polyethylene, polypropylene and multipolymer thereof, in hot-work and life-time service, is subject to the effect of light and heat, can be by airborne dioxygen oxidation, and the mechanical properties of polymer forfeiture, it is not attractive in appearance that outward appearance becomes.Therefore need to add oxidation inhibitor, to improve polyolefinic thermostability.
Long-chain N, N-dialkyl group oxyamine is known to be a kind of effective oxidation inhibitor, but when it uses separately in polyolefine, to polyolefinic resisting ageing for long time performance and anti-yellowing property solve bad.
Summary of the invention
In order to address the above problem, the object of the present invention is to provide a kind of composition that the thermostability of excellence can be provided for polyolefine.
The technical solution used in the present invention is: a kind of composition that thermostability is provided for polyolefine, and by N, N-dialkyl group oxyamine and N, the mixture of N-dialkylamine, hindered phenol, phosphorous acid ester and stearate form; The mass ratio of each raw material is as follows,
N, N-dialkyl group oxyamine and N, the mixture of N-dialkylamine: hindered phenol: phosphorous acid ester: stearate=0.05-0.2:1:2-3:0.5-1.
Described N, the structural formula of N-dialkylamine are R
1R
2NH, N, the structural formula of N-dialkyl group oxyamine is R
1R
2NOH, wherein, R
1And R
2Identical or different, be the alkyl of 12 to 30 carbon.
N, N-dialkyl group oxyamine and N, the preparation method of the mixture of N-dialkylamine has following two kinds: (1) with N, N-dialkylamine (R
1R
2NH) be dissolved in the lower alcohol, add aqueous hydrogen peroxide solution, under 40-80 ℃, react after 2-6 hour, underpressure distillation goes out lower alcohol, and the gained solid is N, N-dialkyl group oxyamine (R
1R
2NOH) and N, N-dialkylamine (R
1R
2NH) mixture, R
1R
2NH and R
1R
2R in the NOH mixture
1R
2The NH quality is less than 10%.(2) with N, N-dialkylamine (R
1R
2NH) be dissolved in the lower alcohol, add aqueous hydrogen peroxide solution, under 40-80 ℃, react after 2-6 hour, filter under this temperature, and wash solid with the lower alcohol under this temperature, filter cake is N, N-dialkyl group oxyamine (R
1R
2NOH); Filtrate is merged rear underpressure distillation, and the product after the underpressure distillation is N, N-dialkyl group oxyamine and N, the mixture of N-dialkylamine, R
1R
2NH and R
1R
2R in the NOH mixture
1R
2The NH quality is less than 20%.Described lower alcohol is the alkyl alcohol less than six carbon, comprises one or more mixing of methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, the trimethyl carbinol, Pentyl alcohol, primary isoamyl alcohol, n-hexyl alcohol or hexalin.Preferably, lower alcohol is one or more mixing of ethanol, propyl alcohol, Virahol or propyl carbinol.
Above-mentioned a kind of composition that thermostability is provided for polyolefine, described hindered phenol is selected from four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, β-(3, the 5-di-tert-butyl-hydroxy phenyl) the positive octadecanol ester of propionic acid or 1,3,5-trimethylammonium-2,4, the combination of one or more of 6-three (3,5-di-tert-butyl-4-hydroxyl benzyl) benzene.Preferably, hindered phenol is four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester.
Above-mentioned a kind of composition that thermostability is provided for polyolefine, described phosphorous acid ester are selected from one or both the mixing of three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid esters or two (2,4-DTBP) pentaerythritol diphosphites.Preferably, phosphorous acid ester is three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester.
Above-mentioned a kind of composition that thermostability is provided for polyolefine, described stearate are selected from one or more mixing of calcium stearate, Zinic stearas or Magnesium Stearate.Preferably, stearate is calcium stearate.
Above-mentioned a kind of composition that thermostability is provided for polyolefine, described polyolefine refer to polyethylene or polyacrylic homopolymer or its multipolymer.Preferably, polyolefine is homopolymer polypropylene.
Composition of the present invention is as oxidation inhibitor, and the add-on in polyolefine processing is 800-3000ppm.Especially, the add-on of composition in polyolefine is 800-1800ppm.Composition of the present invention can join in the polyolefine by powder type.Also can join in the polyolefine through forming particle after the granulation.
N of the present invention, N-dialkyl group oxyamine and N, the preparation method of the mixture of N-dialkylamine, first method is simple, does not have still residual, and all raw materials all utilize, and the cost of product is very low.N in the product, the content of N-dialkylamine is not more than 10%.Second method can obtain pure N, N-dialkyl group oxyamine and N, and N-dialkyl group oxyamine and N, the mixture of N-dialkylamine, N in the mixture, the content of N-dialkylamine is not more than 20%.Among the second preparation method, the filter cake that obtains is highly purified N, and N-dialkyl group oxyamine can use as oxidation inhibitor separately.
N in the composition of the present invention, N-dialkyl group oxyamine Wheat Protein, N, the N-dialkylamine has the effect of acid scavenger.N, N-dialkylamine are typical alkaline compounds, can with residual Cl in the pp material
-Ionic reaction can play the effect of deacidification.N, N-dialkyl group oxyamine and N, the mixture of N-dialkylamine can be used as the antioxygen acid scavenger.
Yet, N, N-dialkyl group oxyamine and N, when N-dialkylamine mixture uses separately, its antioxidant effect can't satisfy polyolefinic service requirements fully, when jointly using with hindered phenol antioxygen, phosphorous acid ester auxiliary anti-oxidant and a certain amount of acid scavenger, can provide excellent thermal oxidation stability habit for polyolefine.
The invention has the beneficial effects as follows: N, N-dialkyl group oxyamine and N, the mixture cost of N-dialkylamine is low, has simultaneously antioxygen deacidification effect, when jointly using with hindered phenol antioxygen, phosphorous acid ester auxiliary anti-oxidant and a certain amount of acid scavenger, can provide excellent thermo-oxidative stability for polyolefine.
Embodiment
The twin-screw extrusion test: extrude in twin screw extruder, extruder temperature is set as TS1:180 ℃, TS2-TS10:200 ℃.
Homopolymer polypropylene: melting index is 7.3g/10min.
Natene: melting index is 10g/10min.
Test by the following method total amine value:
1, the 50mL Glacial acetic acid adds 0.5g left and right sides sample;
2, add the Viola crystallina indicator, with the HClO of 0.1N
4Be titrated to purple and disappear, be blue.
Calculate: total amine value=(N * V * 56.11)/M
N---HClO
4Equivalent concentration
V---consumption HClO
4Number
M---sample grams
N, N-dialkyl group oxyamine and N, in the N-dialkylamine mixture, N, the content of N-dialkylamine is by the change calculations of total amine value before and after the reaction.
The mixture of 1 pair of hydrogenated-tallow group oxyamine of embodiment and two hydrogenated-tallow group amine
The two hydrogenated-tallow group amine (diamines is greater than 90%) of 10g are dissolved in 60 ℃ the 50mL propyl carbinol, to the hydrogen peroxide that wherein drips 2mL 70%, be added dropwise to complete among the 30min, react after two hours, underpressure distillation goes out propyl carbinol, and solid is carried out vacuum-drying, obtains the mixture of the two hydrogenated-tallow group oxyamines of 10g and two hydrogenated-tallow group amine, wherein, the content of two hydrogenated-tallow group amine is 3%.
The mixture of 2 pairs of hydrogenated-tallow group oxyamines of embodiment and two hydrogenated-tallow group amine
The two hydrogenated-tallow group amine (diamines is greater than 90%) of 10g are dissolved in 60 ℃ the 50mL propyl carbinol, to the hydrogen peroxide that wherein drips 2mL 70%, be added dropwise to complete among the 30min, react after two hours, filter out propyl carbinol, use the 50mL propyl carbinol 60 ℃ of lower washed twice, filter cake by analysis, be the two hydrogenated-tallow group oxyamines of high purity, wherein, two hydrogenated-tallow group amine contents are 0.2%.Filtrate is merged, underpressure distillation goes out propyl carbinol, product after the underpressure distillation is the mixture of two hydrogenated-tallow group oxyamines and two hydrogenated-tallow group amine, mixture is carried out vacuum-drying, obtain the mixture of the two hydrogenated-tallow group oxyamines of 5.0g and two hydrogenated-tallow group amine, the content of two hydrogenated-tallow group amine is 16%.
3 one kinds of compositions that thermostability is provided for polyolefine of embodiment
With two hydrogenated-tallow group oxyamines of embodiment 1 preparation and mixture, the four [β-(3 of two hydrogenated-tallow group amine, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester and calcium stearate, 0.11:1:2.22:0.83 mixes and makes in mass ratio.
It is mixed with powder, join in the polypropylene, add-on is 1500ppm, in screw rod, extrude three times after, polypropylene melt index is 9.3 g/10min, yellowness index is 3.5.
Embodiment 4
A kind of composition that thermostability is provided for polyolefine
With two hydrogenated-tallow group oxyamines of embodiment 1 preparation and the mixture of two hydrogenated-tallow group amine, four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester and calcium stearate, 0.18:1:2.35:0.88 mixes and makes in mass ratio.
It is mixed with powder, join in the polypropylene, add-on is 1500ppm, in screw rod, extrude three times after, polypropylene melt index is 10.2 g/10min, yellowness index is 2.5.
Embodiment 5
A kind of composition that thermostability is provided for polyolefine
With two hydrogenated-tallow group oxyamines of embodiment 1 preparation and the mixture of two hydrogenated-tallow group amine, four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester and calcium stearate, 0.05:1:2.1:0.79 mixes and makes in mass ratio.
It is mixed with powder, join in the polypropylene, add-on is 1500ppm, in screw rod, extrude three times after, polypropylene melt index is 8.7 g/10min, yellowness index is 3.4.
Embodiment 6
A kind of composition that thermostability is provided for polyolefine
With two hydrogenated-tallow group oxyamines of embodiment 2 preparations and the mixture of two hydrogenated-tallow group amine, four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester and calcium stearate, 0.05:1:2.1:0.79 mixes and makes in mass ratio.
It is mixed with powder, join in the polypropylene, add-on is 1200ppm, in screw rod, extrude three times after, polypropylene melt index is 9.3 g/10min, yellowness index is 3.7.
Embodiment 7
A kind of composition that thermostability is provided for polyolefine
With two hydrogenated-tallow group oxyamines of embodiment 2 preparations and the mixture of two hydrogenated-tallow group amine, 1,3,5-trimethylammonium-2,4,6-three (3, the 5-di-tert-butyl-4-hydroxyl benzyl) benzene, two (2,4-DTBP) pentaerythritol diphosphites and Magnesium Stearate form, and make for 0.05:1:2.1:0.79 mixes in mass ratio.
It is mixed with powder, join in the polypropylene, add-on is 1500ppm, in screw rod, extrude three times after, polypropylene melt index is 8.2 g/10min, yellowness index is 1.6.
Embodiment 8
A kind of composition that thermostability is provided for polyolefine
With two hydrogenated-tallow group oxyamines of embodiment 2 preparations and the mixture of two hydrogenated-tallow group amine, β-(3, the 5-di-tert-butyl-hydroxy phenyl) the positive octadecanol ester of propionic acid, three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester and Zinic stearas made for 0.05:1:2.1:0.79 mixes in mass ratio.
It is mixed with powder, join in the polypropylene, add-on is 1000ppm, in screw rod, extrude three times after, polypropylene melt index is 12.6 g/10min, yellowness index is 0.9.
Simultaneous test
Simultaneous test 1
With four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester, calcium stearate forms, and 1:2.22:0.83 mixes and makes in mass ratio.
It is mixed with powder, join in the polypropylene, add-on is 1500ppm, in screw rod, extrude three times after, polypropylene melt index is 12.3 g/10min, yellowness index is 4.1.
Simultaneous test 2
The mixture of embodiment 1 preparation is joined in the polypropylene powder, and add-on is 400ppm, in screw rod, extrude three times after, polypropylene melt index is 23.9 g/10min, yellowness index is 5.9.
By above-mentioned simultaneous test as can be known, composition of the present invention is excellent antioxidant system, can the polyolefinic thermostability of Effective Raise.
Claims (10)
1. composition that thermostability is provided for polyolefine is characterized in that: by N, and N-dialkyl group oxyamine and N, the mixture of N-dialkylamine, hindered phenol, phosphorous acid ester and stearate form; The mass ratio of each raw material is as follows:
N, N-dialkyl group oxyamine and N, the mixture of N-dialkylamine: hindered phenol: phosphorous acid ester: stearate=0.05-0.2:1:2-3:0.5-1;
Described N, the structural formula of N-dialkylamine are R
1R
2NH, N, the structural formula of N-dialkyl group oxyamine is R
1R
2NOH, wherein, R
1And R
2Identical or different, be the alkyl of 12 to 30 carbon.
2. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 1, it is characterized in that: described N, N-dialkyl group oxyamine and N, the preparation method of the mixture of N-dialkylamine is as follows:
With N, the N-dialkylamine is dissolved in the lower alcohol, adds aqueous hydrogen peroxide solution, under 40-80 ℃, react after 2-6 hour, underpressure distillation goes out lower alcohol, and the gained solid is N, N-dialkyl group oxyamine and N, the mixture of N-dialkylamine, wherein, N, N-dialkylamine quality is less than 10%; Or,
With N, the N-dialkylamine is dissolved in the lower alcohol, adds aqueous hydrogen peroxide solution, under 40-80 ℃, reacts after 2-6 hour, filters under this temperature, and washs solid with the lower alcohol under this temperature, and filter cake is N, N-dialkyl group oxyamine; Filtrate is merged rear underpressure distillation, and the product after the underpressure distillation is N, N-dialkyl group oxyamine and N, and the mixture of N-dialkylamine, wherein, and N, N-dialkylamine quality is less than 10%.
3. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 2, it is characterized in that described lower alcohol is one or more mixing of methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, the trimethyl carbinol, Pentyl alcohol, primary isoamyl alcohol, n-hexyl alcohol or hexalin.
4. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 1, it is characterized in that: described hindered phenol is selected from four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, β-(3, the 5-di-tert-butyl-hydroxy phenyl) the positive octadecanol ester of propionic acid or 1,3,5-trimethylammonium-2,4, the combination of one or more of 6-three (3,5-di-tert-butyl-4-hydroxyl benzyl) benzene.
5. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 4, it is characterized in that: described hindered phenol is four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester.
6. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 1, it is characterized in that: described phosphorous acid ester is selected from one or both the mixing of three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid esters or two (2,4-DTBP) pentaerythritol diphosphites.
7. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 6, it is characterized in that: described phosphorous acid ester is three ［ 2.4-di-tert-butyl-phenyl ］ phosphorous acid ester.
8. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 1, it is characterized in that: described stearate is selected from one or more mixing of calcium stearate, Zinic stearas or Magnesium Stearate.
9. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 8, it is characterized in that: described stearate is calcium stearate.
10. according to a kind of composition that thermostability is provided for polyolefine claimed in claim 1, it is characterized in that: described polyolefine refers to polyethylene or polyacrylic homopolymer or its multipolymer.
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| CN201210423891.2A CN102942725B (en) | 2012-10-31 | 2012-10-31 | A kind ofly provide the composition of thermostability for polyolefine |
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|---|---|---|---|
| CN201210423891.2A CN102942725B (en) | 2012-10-31 | 2012-10-31 | A kind ofly provide the composition of thermostability for polyolefine |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104419015B (en) * | 2013-09-03 | 2017-06-09 | 中国科学院化学研究所 | A kind of composition and its application that heat endurance is provided for polymer |
| CN107254085A (en) * | 2017-06-20 | 2017-10-17 | 北京吉海川科技发展有限公司 | A kind of polyolefin assistant composition with high antioxygenic property |
| CN110637053A (en) * | 2017-05-25 | 2019-12-31 | 切弗朗菲利浦化学公司 | Method for improving color stability of polyethylene resin |
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|---|---|---|---|---|
| EP0286596A2 (en) * | 1987-04-10 | 1988-10-12 | Ciba-Geigy Ag | Use of n,n-dialkylhydroxylamines and their preparation |
| US4876300A (en) * | 1987-12-30 | 1989-10-24 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with long chain N,N-dialkylhydroxylamines |
| CN1272863A (en) * | 1998-06-12 | 2000-11-08 | 蒙岱尔北美股份有限公司 | Olefin polymer composition having low smoke generation and fiber, film and fabric prepared therefrom |
-
2012
- 2012-10-31 CN CN201210423891.2A patent/CN102942725B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0286596A2 (en) * | 1987-04-10 | 1988-10-12 | Ciba-Geigy Ag | Use of n,n-dialkylhydroxylamines and their preparation |
| US4876300A (en) * | 1987-12-30 | 1989-10-24 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with long chain N,N-dialkylhydroxylamines |
| CN1272863A (en) * | 1998-06-12 | 2000-11-08 | 蒙岱尔北美股份有限公司 | Olefin polymer composition having low smoke generation and fiber, film and fabric prepared therefrom |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104419015B (en) * | 2013-09-03 | 2017-06-09 | 中国科学院化学研究所 | A kind of composition and its application that heat endurance is provided for polymer |
| CN110637053A (en) * | 2017-05-25 | 2019-12-31 | 切弗朗菲利浦化学公司 | Method for improving color stability of polyethylene resin |
| US11401405B2 (en) | 2017-05-25 | 2022-08-02 | Chevron Phillips Chemical Company Lp | Methods for improving color stability in polyethylene resins |
| CN107254085A (en) * | 2017-06-20 | 2017-10-17 | 北京吉海川科技发展有限公司 | A kind of polyolefin assistant composition with high antioxygenic property |
| CN107254085B (en) * | 2017-06-20 | 2020-09-25 | 北京吉海川科技发展有限公司 | Polyolefin auxiliary agent composition with high oxidation resistance |
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