CN106977668B - Method for preparing polar monomer modified polyolefin-g-polystyrene graft - Google Patents
Method for preparing polar monomer modified polyolefin-g-polystyrene graft Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
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Abstract
The invention provides a process for preparing polar monomer modified polyolefin-g-polystyrene, belonging to the field of polymer science. The invention mainly comprises three steps: 1) preparing a polyolefin-g-polystyrene compatibilization master batch: preparing a polyolefin/polystyrene compatibilization master batch with high content of polyolefin-g-polystyrene by taking Lewis acid as a catalyst and utilizing Friedel-Crafts alkylation reaction; 2) extracting and separating the polyolefin-g-polystyrene graft by a solvent; 3) mixing the polyolefin-g-polystyrene graft with a polar monomer, a grafting assistant agent and an initiator, and reacting in a reaction kettle or mixing equipment to prepare the graft of the polar monomer modified polyolefin-g-polystyrene. The obtained graft has higher application value in the aspects of multi-polymer compatibilization modification, hybrid waste plastic recovery and the like.
Description
Technical Field
The invention belongs to the field of high polymer material reaction processing, and relates to a preparation method of a novel graft. In particular to a method for preparing a polar monomer modified Polyolefin (PO) -g-Polystyrene (PS) graft by using a melt grafting technology.
Background
The functionalization of the polymer is the key point of research and development for decades, and particularly, polar monomer modified polyolefin products have wide application in the aspects of blending compatibilization, filling reinforcement, modified engineering plastics, adhesive composite materials and the like, so that the wetting, bonding, printing and coating performances of the polyolefin are greatly improved. In recent years, new grafting processes and new grafting monomers have been sought and many patents have been filed. However, the application range of the polar monomer modified polyolefin prepared by the method is limited, and particularly, the compatibilization effect of the polar monomer modified polyolefin is limited when waste hybrid plastics such as polyolefin, polystyrene and engineering plastics are recycled. If the polar monomer modified PO-g-PS graft can be prepared, the method has important significance for compatibilization of the ternary incompatible blends or recovery of mixed waste plastics. The invention carries out Friedel-Crafts alkylation reaction on Polyolefin (PO) and Polystyrene (PS) under proper conditions, extracts reaction products, separates unreacted PO and PS, finally mixes pure PO-g-PS and polar monomer according to proper proportion, and reacts at certain temperature and rotation speed through blending equipment to prepare the polar monomer modified PO-g-PS graft.
Disclosure of Invention
The invention provides a novel method for modifying Polyolefin (PO) -g-Polystyrene (PS) graft by polar monomer, which has important significance for the blending and compatibilization of ternary incompatible polymers such as polyolefin, polystyrene, engineering plastics and the like, the recycling of mixed waste plastics and the like. The invention combines Friedel-Crafts alkylation reaction between polyolefin and polystyrene and polar monomer grafting polyolefin reaction to prepare a novel graft-polar monomer modified PO-g-PS graft.
The invention provides a novel method for preparing polar monomer modified Polyolefin (PO) -g-Polystyrene (PS), which mainly comprises three steps:
1) preparation of PO/PS compatibilized masterbatch:
and (2) adding a mixture of PO and PS into an internal mixer (an extruder and an open mill), wherein the PO can be HDPE, LDPE, LLDPE, EPDM, POE and the like, and the using amount of the PO and PS mixed resin is 30-70% of the total mass of the PO and PS mixed resin. Preferably 40 to 60%. The Lewis acid catalyst is AlCl3、AlI3、AlBr3、SnCl4、FeCl3、SnCl4、ZnCl2、InCl3、 InBr3、NiCl2Trimethylchlorosilane or dimethylsilane
One or more of chlorosilane; the using amount of the mixed resin is 0.2-2.0% of the total mass of the mixed resin. The optimal reaction conditions are temperature: 120-150 ℃; time: 4-10 minutes; the rotating speed is 30-60 r/min.
2) Separating out pure PO-g-PS graft through solvent extraction;
repeatedly extracting with ethyl acetate, acetone or their mixture to separate unreacted PS; and repeatedly extracting by using n-heptane to separate unreacted PO so as to finally obtain the pure PO-g-PS graft.
3) Polar monomer modified PO-g-PS graft
The PO-g-PS graft (or PO/PS compatibilized master batch), the polar monomer, the grafting assistant agent, the initiator and the like react under certain equipment and conditions to prepare the novel polar monomer modified PO-g-PS graft (or PO/PS compatibilized master batch). Wherein the graftable polar monomer is selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, itaconic anhydride, maleic anhydride, substituted maleic anhydride, monosodium maleate, disodium maleate, acrylamide, maleimide, glycidyl methacrylate, diethyl fumarate, vinyltrimethoxysilane and vinyltriethoxysilane, and 1-acrylamidopyrrolidine-2-carboxylic acid, 2-acrylamidoacetic acid, 2-acrylamidopropionic acid and 2-acrylamido-3-methylbutyric acid, and the like. The amount is 5-15% of the weight of the PO-g-PS graft.
The initiator is one or more of dicumyl peroxide (DCP), 2, 5-dimethyl-2, 5-bis (tert-butylperoxy) hexane (DTBH) and di-tert-butyl peroxide (DBP); the amount of the PO-g-PS graft is 0.5 to 1.2 percent of the weight of the PO-g-PS graft.
The grafting aid is a monomer having at least one carbon-carbon double bond, and is specifically selected from styrene, diallyl phthalate, diethylene glycol diacrylate, ethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol diacrylate, 1, 3-butanediol dimethacrylate, 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate, propoxylated neopentyl glycol diacrylate, triallyl isocyanurate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol triacrylate, 3) ethoxylated trimethylolpropane triacrylate, (3) propoxylated trimethylolpropane triacrylate, (4) ethoxylated pentaerythritol tetraacrylate, ethylene glycol diacrylate, propylene glycol diacrylate, (3) one or a mixture of more of glycerol oxide triacrylate, pentaerythritol tetraacrylate, di-trimethylolpropane tetraacrylate and dipentaerythritol hexaacrylate. The amount is 4-10% of the weight of PO-g-PS graft.
The equipment and conditions are as follows: injecting a mixture of the polar monomer, the grafting assistant agent and the initiator into a melting section on an extruder by using a metering pump, and controlling the adding speed of the mixed material to prepare a polar monomer modified PO-g-PS graft; or PO-g-PS graft, monomer, grafting assistant agent, initiator, etc. through direct mixing and extrusion. The temperature of the extruder from the hopper to the neck mold is respectively as follows: the first temperature section is 110-125 ℃, the second temperature section is 135-150 ℃, the third temperature section is 160-170 ℃, the fourth temperature section is 180-185 ℃, the fifth temperature section is 185-190 ℃, the temperature of the mouth mold is 140-155 ℃, and the rotating speed of the screw of the extruder is 40-80 r/min. Or dissolving PO-g-PS in a reaction kettle, adding polar monomer, initiator and grafting assistant into the solution, and reacting at 80-160 deg.C for 1-2 hr.
Detailed Description
The LDPE referred to in the following examples is low density polyethylene of Shanghai petrochemical grade No. N220 having MFR of 2.2g/10min (190 ℃, 2.16 Kg); HDPE is high density polyethylene with a mark of 5000S produced by petrochemical production of a winnowing, and MFR is 0.8-1.3 g/10min (190 ℃, 2.16 Kg); LLDPE is linear low density polyethylene with 7042 trade mark produced by petrochemical of a pump, and MFR is 1.7-2.3 g/10min (190 ℃, 2.16 Kg); EPDM is a 3720P ethylene propylene diene monomer produced by DuPont Dow, and the propylene content is 30 wt%; POE is an ethylene propylene copolymer produced by DuPont Dow under the trade name 8003, and MFR is 1g/10min (190 ℃, 2.16 Kg); PS is polystyrene of grade GPPS525 produced by Jiangsu Laiton, MFR is 7g/10min (210 ℃, 2.16 Kg); AlCl3The product is sold by chemical industry in Temple east of continuous cloud port, and the purity is more than 99%; FeCl3Is sold by Nanjing Noria chemical company, and has a purity of over 99 percent; DCP and DTBH are produced by Shanghai Qin Feng chemical company, and the purity is more than 99 percent; MAH is produced by national pharmaceutical chemistry group limited company, and the purity is more than 99 percent; GMA is produced by Jiangxi Ruixiang chemical industry Co., Ltd, and the purity is more than 99%; DAP is produced by Suoguanno union chemical industry Co., Ltd, and the purity is more than 95%; st, MAA, AA, and ITA are produced by Shanghai Lingfeng chemical Co., Ltd, and have a purity of 99% or more.
Example one
Mixing 700g of LDPE, 300gPS and 3g of AlCl3And banburying in an internal mixer at 140 deg.C for 6min to obtain LDPE/PS (70/30) grafted masterbatch, and repeatedly extracting the grafted masterbatch with n-heptane and ethyl acetate to obtain pure LDPE-g-PS.
Putting 300g of pure LDPE-g-PS into an extruder, accurately weighing 20g of Maleic Anhydride (MAH), 1.5g of dicumyl peroxide (DCP) and 20g of styrene (St), dissolving the materials in acetone, injecting the dissolved materials into a metering pump, injecting the dissolved materials into an extruder in an extrusion melting section, and carrying out extrusion granulation to obtain (LDPE-g-PS) -g-MAH, wherein the temperature of the extruder from a hopper to a neck mold during granulation is respectively as follows: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min.
Example two
500g of LDPE, 500gPS, 3g of AlCl3And banburying in an internal mixer at 140 deg.C for 6min to obtain LDPE/PS (50/50) grafted masterbatch, and repeatedly extracting the grafted masterbatch with n-heptane and ethyl acetate to obtain pure LDPE-g-PS.
Putting 300g of pure LDPE-g-PS into an extruder, accurately weighing 30g of Maleic Anhydride (MAH), 2g of dicumyl peroxide (DCP) and 30g of styrene (St), dissolving the materials with acetone, injecting the dissolved materials into a metering pump, injecting the dissolved materials into the extruder in an extrusion melting section, and carrying out extrusion granulation to obtain (LDPE-g-PS) -g-MAH, wherein the temperature of the extruder from a hopper to a neck mold during granulation is respectively as follows: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min.
Example three
500g of LLDPE, 500gPS, 3g of FeCl3And banburying in an internal mixer at 140 deg.C for 6min to obtain LLDPE/PS (50/50) grafted mother material, and repeatedly extracting the grafted mother material with n-heptane and ethyl acetate to obtain pure LLDPE-g-PS.
Putting 300g of pure LLDPE-g-PS into an extruder, accurately weighing 20g of Acrylic Acid (AA), 1.5g of dicumyl peroxide (DCP) and 20g of styrene (St), dissolving the materials in acetone, injecting the dissolved materials into a metering pump, injecting the dissolved materials into the extruder in an extrusion melting section, and carrying out extrusion granulation to obtain (LLDPE-g-PS) -g-AA, wherein the temperatures of the extruder from a hopper to a neck ring die during granulation are respectively as follows: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min.
Example four
500g HDPE, 500gPS, 3g AlCl3And banburying in an internal mixer at 120 deg.C for 6min to obtain LDPE/PS (50/50) grafted masterbatch, and repeatedly extracting the grafted masterbatch with n-heptane and ethyl acetate to obtain pure HDPE-g-PS.
Putting 300g of pure HDPE-g-PS into an extruder, accurately weighing 30g of Maleic Anhydride (MAH), 2g of dicumyl peroxide (DCP) and 30g of styrene (St), dissolving the materials with acetone, injecting the materials into a metering pump, injecting the materials into the extruder in an extrusion melting section, and carrying out extrusion granulation to obtain (HDPE-g-PS) -g-MAH, wherein the temperatures of the extruder from a hopper to a neck mold during granulation are respectively: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min.
Example five
500g of LLDPE, 500gPS, 3g of AlCl3And banburying in an internal mixer at 140 deg.C for 6min to obtain LLDPE/PS (50/50) grafted mother material, and repeatedly extracting the grafted mother material with n-heptane and ethyl acetate to obtain pure LLDPE-g-PS.
Putting 300g of pure LLDPE-g-PS into an extruder, accurately weighing 30g of Glycidyl Methacrylate (GMA), 2.5g of dicumyl peroxide (DCP) and 30g of styrene (St), dissolving the materials in acetone, injecting the dissolved materials into a metering pump, injecting the dissolved materials into an extruder at an extrusion melting section, and carrying out extrusion granulation to obtain (LLDPE-g-PS) -g-GMA, wherein the temperatures of the extruder from a hopper to a neck mold during granulation are respectively as follows: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min.
Example six
500g POE, 500gPS, 3g AlCl3And banburying in an internal mixer at 140 ℃ for 6min to obtain POE/PS (50/50) grafted master batch, and repeatedly extracting the grafted master batch with n-heptane and ethyl acetate respectively to obtain pure POE-g-PS.
Putting 300g of pure POE-g-PS into an extruder, accurately weighing 30g of methacrylic acid (MAA), 1.5g of 2, 5-dimethyl-2, 5-bis (tert-butylperoxy) hexane (DTBH) and 30g of styrene (St), dissolving the materials in acetone, injecting the dissolved materials into a metering pump, injecting the dissolved materials into the extruder at an extrusion melting section, and carrying out extrusion granulation to obtain (POE-g-PS) -g-MAA, wherein the temperatures of the extruder from a hopper to a neck ring mold during granulation are respectively: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min.
Example seven
500g of LDPE, 500gPS, 3g of AlCl3And banburying in an internal mixer at 140 deg.C for 6min to obtain LDPE/PS (50/50) grafted masterbatch, and repeatedly extracting the grafted masterbatch with n-heptane and ethyl acetate to obtain pure LDPE-g-PS.
Putting 300g of pure LDPE-g-PS into an extruder, accurately weighing 30g of Glycidyl Methacrylate (GMA), 2g of dicumyl peroxide (DCP) and 30g of diallyl phthalate (DAP), dissolving the materials with acetone, injecting the dissolved materials into a metering pump, injecting the dissolved materials into an extruder in an extrusion melting section, and carrying out extrusion granulation to obtain (LDPE-g-PS) -g-GMA, wherein the temperature of the extruder from a hopper to a neck mold during granulation is respectively as follows: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min.
Example eight
500g EPDM, 500gPS, 3g AlCl3Adding into an internal mixer, banburying at 140 deg.C for 6min to obtain EPDM/PS (50/50) graft master batch, and repeatedly extracting the graft master batch with n-heptane and ethyl acetate to obtain pure EPDM-g-PS.
100g of EPDM-g-PS is put into a reaction kettle and dissolved by excessive xylene, 10g of Maleic Anhydride (MAH), 0.5g of dibenzoyl peroxide (BPO) and 10g of styrene (St) are added to react for 1.5h at 80 ℃ to obtain (EPDM-g-PS) -g-MAH.
Example nine
500g of LDPE, 500gPS, 3g of AlCl3And (3) putting the mixture into an internal mixer for internal mixing for 6min at the temperature of 140 ℃ to obtain the LDPE/PS (50/50) grafted master batch.
300g of pure LDPE-g-PS is put into an extruder, 40g of itaconic acid (ITA), 2.5g of dicumyl peroxide (DCP) and 40g of styrene (St) are accurately weighed, dissolved by acetone and injected into a metering pump, and injected into the extruder at an extrusion melting section for extrusion and granulation to obtain the anhydride grafting master batch. The temperature of the extruder from the hopper to the mouth mold during granulation is respectively as follows: the first temperature section is 120 ℃, the second temperature section is 150 ℃, the third temperature section is 170 ℃, the fourth temperature section is 185 ℃, the fifth temperature section is 190 ℃, the temperature of the mouth mold is 150 ℃, and the rotating speed of the screw of the extruder is 60 r/min. The obtained acid anhydride grafting master batch is repeatedly extracted by using n-heptane, ethyl acetate and acetone respectively to obtain pure (LDPE-g-PS) -g-ITA.
Attached table 1
In the table, the grafting ratio of PS refers to the mass of PS on the graft as a percentage of the charged amount of PS, and the grafting ratio of polar monomer refers to the mass of polar monomer on the graft as a percentage of the mass of modified graft.
The new method for preparing the polar monomer modified PO-g-PS graft provided by the invention is described in detail above. The principles and embodiments of the present invention have been described herein using specific examples, which are presented only to assist in understanding the method and its core concepts of the present invention. It should be noted that, for those skilled in the art, without departing from the principle of the present invention, several improvements and modifications can be made to the present invention, and these improvements and modifications also fall into the protection scope of the claims of the present invention.
Claims (5)
1. A process for preparing a polar monomer-modified Polyolefin (PO) -g-Polystyrene (PS) comprising three steps:
1) preparation of PO/PS compatibilized masterbatch: in a mixing device, under the conditions that the temperature is 120-;
2) separating out PO-g-PS graft through solvent extraction;
3) injecting a mixture of the polar monomer, the grafting assistant agent and the initiator into a melting section on an extruder by using a metering pump, and controlling the adding speed of the mixed material to prepare a polar monomer modified PO-g-PS graft; or PO-g-PS graft, monomer, grafting assistant agent and initiator, and directly mixing and extruding; the temperature of the extruder from the hopper to the neck mold is respectively as follows: the first temperature section is 110-125 ℃, the second temperature section is 135-150 ℃, the third temperature section is 160-170 ℃, the fourth temperature section is 180-185 ℃, the fifth temperature section is 185-190 ℃, the temperature of a mouth mold is 140-155 ℃, the screw rotating speed of the extruder is 40-80 revolutions per minute, and the polar monomer modified Polyolefin (PO) -g-Polystyrene (PS) is prepared; or dissolving PO-g-PS solvent in a reaction kettle, adding polar monomer, initiator and grafting assistant agent into the solution, reacting for 1-2 hours at 80-180 ℃, and separating and purifying to obtain the polar monomer modified Polyolefin (PO) -g-Polystyrene (PS).
2. The method for preparing a polar monomer modified PO-g-PS graft as claimed in claim 1, wherein in the step (1), the Polyolefin (PO) comprises one or more of HDPE, LDPE, LLDPE, EPDM and POE, and the amount is 30-70% of the total mass of the PO and PS mixed resin; the Lewis acid is AlCl3、AlI3、AlBr3、SnCl4、FeCl3、ZnCl2、InCl3、InBr3、NiCl2One or more of trimethylchlorosilane or dimethylchlorosilane, wherein the using amount of the one or more of trimethylchlorosilane or dimethylchlorosilane is 0.2-2.0% of the total mass of the mixed resin.
3. The method for preparing a polar monomer-modified PO-g-PS graft according to claim 1, characterized in that the graftable polar monomer of step (3) is selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, itaconic anhydride, maleic anhydride, substituted maleic anhydride, monosodium maleate, disodium maleate, acrylamide, maleimide, glycidyl methacrylate, diethyl fumarate, vinyltrimethoxysilane and vinyltriethoxysilane, and one or more of 1-acryloyl pyrrolidine-2-carboxylic acid, 2-acrylamide acetic acid, 2-acrylamide propionic acid and 2-acrylamide-3-methyl butyric acid, wherein the dosage is 5-15% of the weight of the PO-g-PS graft.
4. The method for preparing a polar monomer modified PO-g-PS graft according to claim 1, wherein the initiator in step (3) is one or more selected from dicumyl peroxide (DCP), 2, 5-dimethyl-2, 5-bis (t-butylperoxy) hexane (DTBH), di-t-butyl peroxide (DBP); the amount of the PO-g-PS graft is 0.5 to 1.2 percent of the weight of the PO-g-PS graft.
5. The method for preparing a polar monomer-modified PO-g-PS graft according to claim 1, wherein the grafting aid in step (3) is a monomer having at least one carbon-carbon double bond, and is selected from the group consisting of styrene, diallyl phthalate, diethylene glycol diacrylate, ethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol diacrylate, 1, 3-butanediol dimethacrylate, 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate, propoxylated neopentyl glycol diacrylate, triallyl isocyanurate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol diacrylate, propylene glycol diacrylate, and mixtures thereof, (3) Ethoxylated trimethylolpropane triacrylate, (3) propoxylated trimethylolpropane triacrylate, (4) ethoxylated pentaerythritol tetraacrylate, (3) propoxylated glycerol triacrylate, pentaerythritol tetraacrylate, di-trimethylolpropane tetraacrylate and dipentaerythritol hexaacrylate, in an amount of 5-15% by weight of the PO-g-PS graft.
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| US3894119A (en) * | 1971-11-16 | 1975-07-08 | British Petroleum Co | Graft copolymers of polystyrene and polyisobutylene |
| CN104817772A (en) * | 2015-04-17 | 2015-08-05 | 常州大学 | New waste expanded polystyrene recycling method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3894119A (en) * | 1971-11-16 | 1975-07-08 | British Petroleum Co | Graft copolymers of polystyrene and polyisobutylene |
| CN104817772A (en) * | 2015-04-17 | 2015-08-05 | 常州大学 | New waste expanded polystyrene recycling method |
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