US20030144415A1 - Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate - Google Patents
Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate Download PDFInfo
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- US20030144415A1 US20030144415A1 US10/058,058 US5805802A US2003144415A1 US 20030144415 A1 US20030144415 A1 US 20030144415A1 US 5805802 A US5805802 A US 5805802A US 2003144415 A1 US2003144415 A1 US 2003144415A1
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- elastomer
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/005—Processes for mixing polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/16—Ethene-propene or ethene-propene-diene copolymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/04—Crosslinking with phenolic resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/005—Drying oils
Definitions
- the invention relates to a process for the preparation of a thermoplastic elastomer.
- thermoplastic elastomers A process for the preparation of thermoplastic elastomers is for example known from “Compounding of rubber Concentrate Thermoplastic Vulcanizates” by Terry M. Finerman, Ph.D., Luc Vandendriessche, Joseph E. Pfeiffer, presented at the Society of Plastics Engineers Topical Conference TPEs 2000, Sep. 28-29, 1999. Described is the preparation of fully vulcanized rubber concentrates and of thermoplastic elastomers by melt mixing the fully vulcanized rubber concentrates with ingredients such as oil, filler, stabilizers, processing aids and thermoplastic polymers for example polypropylene or polyethylene.
- thermoplastic elastomers have the disadvantage that their mechanical properties are not sufficient for some applications for example in automotive, building and construction, mechanical rubber goods or consumer products. For example the tensile strength value of those thermoplastic elastomers is relatively low and therefore not meeting the required automotive material specifications.
- Another disadvantage of the above process is that the preparation of fully cured rubber concentrates with consistent properties and good morphology is difficult because of the high concentration of elastomeric phase and the minor concentration of thermoplastic phase.
- the object of the present invention is to completely or largely eliminate the stated drawbacks.
- thermoplastic elastomer is prepared by melt mixing:
- the process of the present invention provides the preparation of thermoplastic elastomers with improved mechanical properties which meet the stringent material specifications needed for some applications in automotive, building and construction, mechanical rubber goods or consumer products.
- a further advantage is that the elastic properties of the thermoplastic elastomer are improved.
- the thermoplastic elastomers show an improved fluid resistance.
- thermoplastic elastomers may be prepared with a better compression set.
- the partially vulcanized rubber concentrate (a) is prepared by melt mixing:
- thermoplastic polymer At least one thermoplastic polymer
- thermoplastic polymer(s) melt mixed and kneaded above the melting point of the thermoplastic polymer whereby the elastomer is vulcanized during mixing and kneading. This process is also known as a dynamic vulcanization process.
- the elastomer (e) may be any elastomer capable of being vulcanized by the curing agent.
- elastomer(s) are ethylene-propylene copolymers, hereinafter called EPM, ethylene-propylene-diene terpolymers, hereinafter called EPDM, acrylonitrile-butadiene rubber, styrene-butadiene rubber, isobutene-isoprene rubber, styrene-ethylene/styrene-butadiene block copolymers, butyl rubber, isobutylene-p-methylstyrene copolymers or brominated isobutylene-p-methylstyrene copolymers or natural rubber.
- the elastomer in the partially vulcanized rubber concentrate according to the invention is an olefinic elastomer. It is especially preferred to use EPM or EPDM as elastomer. More preferably, EPDM is used as elastomer.
- the EPDM preferably contains 50-70 parts by weight ethylene monomer units, 48-30 parts by weight alpha-olefin monomer units and 1-12 parts by weight monomer units originating from a non-conjugated diene or combinations of more than one non-conjugated diene.
- the alpha-olefin is propylene.
- non-conjugated diene use is preferably made of dicyclopentadiene (DCPD), 5-ethylidene-2- norbornene (ENB) or vinylnorbornene (VNB).
- DCPD dicyclopentadiene
- ENB 5-ethylidene-2- norbornene
- VNB vinylnorbornene
- the elastomer(s) may be prepared for example with a Ziegler-Natta catalyst, a metallocene catalyst or a single site catalyst.
- the elastomer for example comprises between 0-250 parts of oil per 100 parts of elastomer. Preferably comprises between 20-200 parts per 100 parts of elastomer. It is especially preferred to comprise between 30-160 parts of oil per 100 parts of elastomer.
- Any known oil may be used, examples of oils are processing oils for example paraffinic, naphtalenic or aromatic oil or isoparaffinic oil which is also known as polyalfaolefinic oil.
- a highly hydrogenated oil obtained by a hydrocracking and isodewaxing process is used, for example PennzUltra, 1199, supplied by Pennzoil in the United States of America. The point in time at which the oil is metered is not critical.
- the oil is for example added before, during or after the dynamic vulcanisation of the elastomer. It is also possible that the oil is added partly before and partly during and/or after the dynamic vulcanisation of the elastomer. It is also possible that the elastomer has been pre-mixed with the desired quantity of oil or a proportion thereof. In fact a person skilled in the art can adjust the ratio of elastomer(s)/thermoplastic polymer(s)/oil to achieve partially vulcanized rubber concentrates with a low hardness.
- the partially vulcanized rubber concentrate for example has a hardness of 70 shore A or lower measured according to ASTM D-2240. Preferably the hardness is 60 shore A or lower. Most preferably the hardness is 50 shore A or lower.
- thermoplastic polymers (f) which may be used in the preparation of the partially vulcanized rubber concentrates are thermoplastic polyolefin homo- and copolymers or blends thereof.
- thermoplastic polyolefin homo- and copolymers or blends thereof for example homopolymers of ethylene or propylene, copolymers of ethylene and propylene, copolymers of ethylene and an alpha-olefin comonomer with 4-20 carbon atoms or copolymers of propylene and an alpha-olefin comonomer with 4-20 carbon atoms.
- the content of propylene in said copolymer is preferably at least 75% by weight.
- thermoplastic polyolefin homo- and copolymers may be prepared with a Ziegler-Natta catalyst, a metallocene catalyst or with another single site catalyst.
- suitable thermoplastic polymers are for example reactor thermoplastic polyolefine elastomers (TPO's), polyamides, polycarbonate, polyesters, polysulfones, polylactones, polyacetals, acrylonitrile-butadiene-styrene (ABS) resins, polyphenylene oxide (PPO), polyphenylene sulfide (PPS), styrene-acrylonitrile (SAN) resins, polyimides, styrene maleic anhydride (SMA) and aromatic polyketones. It is possible to use more than one thermoplastic polymer in the preparation of the partially vulcanized rubber concentrates.
- a polypropylene homopolymer is used as thermoplastic polymer.
- the polypropylene may be atactic, isotactic, syndiotactic or a physical and chemical mixture thereof.
- the term chemical mixture means that the polypropylene may have atactic, isotactic or syndiotactic structures randomly or in blocks along the molecular chains.
- the polypropylene homopolymer may be linear or branched.
- the Melt flow index (MFI) of the polypropylene preferably is between 0.3 and 50; more preferably below 20 (according to ISO norm 1133 (230° C.; 2.16 kg load)).
- Suitable curing agents (g) include sulfur, sulfurous compounds, metal oxides, maleimides, phenol resins and peroxides.
- the curing agents may be used with or without accelerators. Said curing agents are for example described in U.S. Pat. No. 5,100,947. It is also possible to use siloxane compounds as curing agent, for example hydrosilane or vinylalkoxysilane.
- the elastomer is preferably vulcanized with a phenol resin, a siloxane or a peroxide.
- Suitable accelerators are sulphur, ethylene dimethylacrylate, polyethylene glycol dimethylacrylate, trimethylol propane trimethacrylate, divinyl benzene, diallyl itaconate, triallyl cyanurate, diallylphtalate, allyl methacrylate, cyclohexyl methacrylate and m-phenylene bismaleimide.
- the amount of curing agent, the accelerator, the temperature and the time of vulcanisation are selected in order to obtain the desired degree of vulcanization.
- the amount of curing agent is between 0.1-10 parts by weight per 100 parts by weight of elastomer. More preferably the amount of curing agent is between 0.1-5 parts by weight per 100 parts by weight of elastomer.
- the degree of vulcanization of the elastomer can be expressed in terms of gel content or conversely, extractable components.
- the gel content is the ratio of the amount of non-soluble elastomer and the total amount of elastomer (in weight) of a specimen soaked in an organic solvent for the elastomer.
- the method is described in U.S. Pat. No.4,311,628 and U.S. Pat. No.5,100,947. In general terms a specimen is soaked for 48 hours in an organic solvent at temperatures suitable for the thermoplastic polymer and the elastomer. The solvent should be capable of dissolving the thermoplastic polymers completely at the temperature of gel test.
- the elastomer in the rubber concentrate is partially vulcanized.
- Partially vulcanized means that the elastomer may be vulcanized to a relatively low degree as long as there is no problem with pellet stickiness.
- the elastomer in the partially vulcanized rubber concentrate has a gel content higher than 50%. More preferably a gel content higher than 70%.
- the partially vulcanized rubber concentrate is preferably prepared by melt mixing between 30-95 parts by weight of the elastomer(s), between 0-70 parts by weight of oil, between 5-50 parts by weight of the thermoplastic polymer(s), between 0.1-10 parts by weight of the curing agent per 100 parts by weight of elastomer, whereby the sum of the parts by weight of the elastomer(s), thermoplastic polymer(s), curing agent and oil is 100.
- the amount of elastomer(s) varies between 35-90 parts by weight, the amount of oil varies between 5-60 parts by weight, the amount of curing agent varies between 0.1-5 parts by weight per 100 parts by weight of elastomer and the amount of thermoplastic polymer(s) varies between 5-40 parts by weight, whereby the sum of the parts by weight of the elastomer(s), thermoplastic polymer(s), curing agent and oil is 100.
- the amount of elastomer(s) varies between 40-85 parts by weight, the amount of oil varies between 10-50 parts by weight, the amount of curing agent is between 0.1-5 parts by weight per 100 parts by weight of elastomer and the amount of thermoplastic polymer(s) varies between 5-30 parts by weight, whereby the sum of the parts by weight of the elastomer(s), thermoplastic polymer(s), curing agent and oil is 100.
- the melt mixing may be carried out in conventional mixing equipment for example roll mills, Banbury mixers, Brabender mixers, continuous mixers for example a single screw extruder, a Buss kneader, Ferro continuous mixer (FCM) and a twin screw extruder.
- melt mixing is carried out in a twin screw extruder with sufficient mixing efficiency, good temperature control and residence time control.
- a twin-screw extruder good tensile properties are achieved.
- the melt mixing is carried out in a single screw extruder.
- By the use of a single screw extruder better compression set values may be achieved.
- the use of a single or twin screw extruder depends on the desired properties the thermoplastic elastomer should have.
- the partially vulcanized rubber concentrate, the thermoplastic polymer and/or the additives, the oil and the curing agent may be dry blended prior to the melt mixing.
- the partially vulcanized rubber concentrate, the thermoplastic polymer and/or the additives, the oil and the curing agent may be directly fed by feeders to the continuous mixer.
- thermoplastic polymers (b) which may be melt mixed with the partially vulcanized rubber concentrate (a) are chosen from the above described thermoplastic polymers (f).
- the choice of the thermoplastic polymer in terms of melt flow index or viscosity depends on the end applications. A person skilled in the art may select the thermoplastic polymer with proper molecular weight, molecular weight distribution or molecular structure to achieve the thermoplastic elastomer with balanced properties.
- processing oils for example paraffinic, naphtalenic or aromatic oil or isoparaffinic oil which is also known as polyalfaolefinic oil.
- a highly hydrogenated oil obtained by a hydrocracking and isodewaxing process is used, for example PennzUltra, 1199, supplied by Pennzoil in the United States of America.
- the point in time at which the oil is metered is not critical.
- the oil is for example added before, during or after the dynamic vulcanisation of the thermoplastic elastomer. It is also possible that the oil is added partly before and partly during and/or after the dynamic vulcanisation of the thermoplastic elastomer.
- the curing agent may be in powder form, in liquid form or may be soluble in a liquid. If the curing agent is in powder form the partially vulcanized rubber concentrate pellets may first be coated with a processing oil and then blended with the curing agent powder prior to melt mixing with the thermoplastic polymers. If the curing agent is in liquid form, it may be dry mixed with the partially vulcanized rubber concentrate prior to melt mixing with the thermoplastic polymer and/or the additives. If the curing agent is soluble in a liquid for example in processing oil or a solvent it may first be dissolved in the liquid and then coated onto the rubber concentrate pellets prior to melt mixing with the thermoplastic polymers. Alternatively, liquid curing agent, curing agent solution in oil or solvent, or curing agent melt can be dosed or injected directly to the mixer in the form of a liquid or liquid solution.
- additives which may be melt mixed are reinforcing and non-reinforcing fillers, plasticizers, antioxidants, stabilizers, processing oil, antistatic agents, waxes, foaming agents, pigments, flame retardants and other known agents described in for example the Rubber World Magazine Blue Book.
- fillers that may be used are calcium carbonate, clay, silica, talc, titanium dioxide, and carbon.
- Another additive that may optionally be used in the thermoplastic elastomer is a Lewis base for example a metal oxide, a metal hydroxide, a metal carbonate or hydrotalcite. The quantity of additive to be added is known to one skilled in the art.
- thermoplastic elastomer by melt mixing the partially vulcanized rubber concentrate, additives and curing agent without the thermoplastic polymer.
- suitable additives are viscosity modifiers, low friction coefficient additives such as silicon oil and fatty amide lubricants, tackifiers or the additives as described above.
- the amount of additives is for example between 0.5-15 parts by weight relative to the total quantity of the thermoplastic elastomer.
- the amount of additives is between 1-10 parts by weight relative to the total quantity of thermoplastic elastomer. More preferably the amount of additives is between 2-8 parts by weight relative to the total quantity of the thermoplastic elastomer.
- the gel content of the thermoplastic elastomer according to the present invention may vary between 60 and 100%.
- the gel content is in excess of 80%. More preferably, the gel content is in excess of 90%. Most preferable the gel content is in excess of 97%.
- the process of the present invention comprises the preparation of the thermoplastic elastomer by melt mixing for example:
- thermoplastic polymer [0038] b. 90-10 parts by weight of a the thermoplastic polymer and/or additives
- thermoplastic elastomer is prepared by melt mixing
- thermoplastic polymer b. 30-85 parts by weight of a the thermoplastic polymer and/or additives
- the process of the present invention may be carried out in two stages.
- the partially vulcanized rubber concentrate may be prepared whereby at least one elastomer is partially vulcanized in the presence of at least one thermoplastic polymer using appropriate curing agents.
- the appropriate thermoplastic polymer and/or additives are melt-mixed in the presence of the curing agent to iniate a further dynamic vulcanization.
- the curing agents used in the first and in the second stage may be the same or different curing agents. Preferably the same curing agent is used in the two stages.
- thermoplastic elastomer may be pelletized.
- the thermoplastic elastomer may however also be directly fed in molten stage to next processing equipment for example through a die.
- the continuous mixer is attached with the die or other necessary downstream equipment and acts not only as mixer but at the same time as a melting and a conveying equipment for processes as foaming, film and sheet extrusion, profile extrusion, film and sheet calendering or co-extrusion.
- the additives may be added during the preparation of the partially vulcanized rubber concentrate or during the preparation of the thermoplastic elastomer or both.
- thermoplastic elastomer prepared by the process according to the present invention may be used in automotive, building and construction, mechanical rubber goods or consumer products.
- Table 1 The properties of compound 1 are shown in table 1.
- Compound 2 was prepared on a 25 mm Berstorff intermeshing co-rotating twin screw extruder.
- compound 3 To prepare compound 3, the compound 1 pellets were first coated with a small amount of processing oil Sunpar 150CTM and then blended with SP1045 powder in a cement mixer before the polypropylene homopolymer 31S07a was introduced. All ingredients were further dry blended using a cement mixer prior to the melt mixing.
- Compound 3 was prepared on a on a 25 mm Berstorff intermeshing co-rotating twin screw extruder.
- thermoplastic elastomer (compound 4) was prepared according to example 3 except that a 1.5 inch Killion single screw extruder with l/d ratio of 24/1 was used.
- melt strands were cooled in a cold water bath before being pelletized. All compounds were dried for at least three hours to remove any residual moisture prior to injection molding.
- Table 2 shows that the thermoplastic elastomers prepared by the process of the present invention have good mechanical properties.
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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US10/058,058 US20030144415A1 (en) | 2002-01-29 | 2002-01-29 | Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate |
US10/501,902 US7572858B2 (en) | 2002-01-29 | 2003-01-28 | Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate |
DE60320635T DE60320635T2 (de) | 2002-01-29 | 2003-01-28 | Verfahren zur herstellung eines thermoplastischen elastomers mit einem teilvulkanisierten kautschukkonzentrat |
JP2003564130A JP4361373B2 (ja) | 2002-01-29 | 2003-01-28 | 部分的に架橋されたゴム濃厚物を含む熱可塑性エラストマーの製造法 |
PCT/NL2003/000057 WO2003064523A1 (en) | 2002-01-29 | 2003-01-28 | Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate |
AT03734917T ATE393797T1 (de) | 2002-01-29 | 2003-01-28 | Verfahren zur herstellung eines thermoplastischen elastomers mit einem teilvulkanisierten kautschukkonzentrat |
EP03734917A EP1470187B1 (de) | 2002-01-29 | 2003-01-28 | Verfahren zur herstellung eines thermoplastischen elastomers mit einem teilvulkanisierten kautschukkonzentrat |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US10/058,058 US20030144415A1 (en) | 2002-01-29 | 2002-01-29 | Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate |
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US20030144415A1 true US20030144415A1 (en) | 2003-07-31 |
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US10/058,058 Abandoned US20030144415A1 (en) | 2002-01-29 | 2002-01-29 | Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate |
US10/501,902 Expired - Fee Related US7572858B2 (en) | 2002-01-29 | 2003-01-28 | Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate |
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US10/501,902 Expired - Fee Related US7572858B2 (en) | 2002-01-29 | 2003-01-28 | Process for the preparation of a thermoplastic elastomer comprising a partially vulcanized rubber concentrate |
Country Status (6)
Country | Link |
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US (2) | US20030144415A1 (de) |
EP (1) | EP1470187B1 (de) |
JP (1) | JP4361373B2 (de) |
AT (1) | ATE393797T1 (de) |
DE (1) | DE60320635T2 (de) |
WO (1) | WO2003064523A1 (de) |
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US20050215717A1 (en) * | 2002-02-11 | 2005-09-29 | Dsm Ip Assets B.V. | Thermoplastic elastomer composition |
US20070043172A1 (en) * | 2003-09-17 | 2007-02-22 | Ellul Maria D | Thermoplastic vulcanizates and processes for making the same |
US20070112132A1 (en) * | 2005-11-16 | 2007-05-17 | Xinyu Zhao | Thermoplastic method, composition, and article |
US20080081879A1 (en) * | 2006-09-29 | 2008-04-03 | Kim Balfour | Crosslinked block copolymer composition and method |
US20080081874A1 (en) * | 2006-09-29 | 2008-04-03 | Kim Balfour | Poly(arylene ether) composition, method, and article |
US7615589B2 (en) | 2007-02-02 | 2009-11-10 | Exxonmobil Chemical Patents Inc. | Properties of peroxide-cured elastomer compositions |
US7625980B2 (en) | 2006-07-11 | 2009-12-01 | Exxonmobil Chemical Patents Inc. | Method for improving extrusion surface smoothness in thermoplastic vulcanizates |
US7875670B2 (en) | 2002-08-12 | 2011-01-25 | Exxonmobil Chemical Patents Inc. | Articles from plasticized polyolefin compositions |
US7985801B2 (en) | 2002-08-12 | 2011-07-26 | Exxonmobil Chemical Patents Inc. | Fibers and nonwovens from plasticized polyolefin compositions |
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US8003725B2 (en) | 2002-08-12 | 2011-08-23 | Exxonmobil Chemical Patents Inc. | Plasticized hetero-phase polyolefin blends |
US8192813B2 (en) | 2003-08-12 | 2012-06-05 | Exxonmobil Chemical Patents, Inc. | Crosslinked polyethylene articles and processes to produce same |
WO2012080159A1 (en) * | 2010-12-14 | 2012-06-21 | Styron Europe Gmbh | Improved elastomer formulations |
US8211968B2 (en) | 2002-08-12 | 2012-07-03 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
US8389615B2 (en) | 2004-12-17 | 2013-03-05 | Exxonmobil Chemical Patents Inc. | Elastomeric compositions comprising vinylaromatic block copolymer, polypropylene, plastomer, and low molecular weight polyolefin |
US8513347B2 (en) | 2005-07-15 | 2013-08-20 | Exxonmobil Chemical Patents Inc. | Elastomeric compositions |
CN109843998A (zh) * | 2016-09-14 | 2019-06-04 | 新橡胶科技控股有限公司 | 来源于脱硫橡胶的热塑性弹性体 |
US11292902B2 (en) | 2018-01-31 | 2022-04-05 | Mcpp Innovation Llc | Modified elastomer composition, crosslinked elastomer composition, and molded article thereof |
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US8217112B2 (en) | 2002-08-12 | 2012-07-10 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
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US8703030B2 (en) | 2003-08-12 | 2014-04-22 | Exxonmobil Chemical Patents Inc. | Crosslinked polyethylene process |
US8192813B2 (en) | 2003-08-12 | 2012-06-05 | Exxonmobil Chemical Patents, Inc. | Crosslinked polyethylene articles and processes to produce same |
US7868096B2 (en) | 2003-09-17 | 2011-01-11 | Exxonmobil Chemical Patents Inc. | Thermoplastic vulcanizates and processes for making the same |
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US20100324161A1 (en) * | 2003-09-17 | 2010-12-23 | Maria Dolores Ellul | Thermoplastic Vulcanizates and Processes for Making the Same |
US20070043172A1 (en) * | 2003-09-17 | 2007-02-22 | Ellul Maria D | Thermoplastic vulcanizates and processes for making the same |
US8389615B2 (en) | 2004-12-17 | 2013-03-05 | Exxonmobil Chemical Patents Inc. | Elastomeric compositions comprising vinylaromatic block copolymer, polypropylene, plastomer, and low molecular weight polyolefin |
US8513347B2 (en) | 2005-07-15 | 2013-08-20 | Exxonmobil Chemical Patents Inc. | Elastomeric compositions |
US7550534B2 (en) | 2005-11-16 | 2009-06-23 | Sabic Innovative Plastics Ip B.V. | Thermoplastic method, composition, and article |
US20070112132A1 (en) * | 2005-11-16 | 2007-05-17 | Xinyu Zhao | Thermoplastic method, composition, and article |
US7625980B2 (en) | 2006-07-11 | 2009-12-01 | Exxonmobil Chemical Patents Inc. | Method for improving extrusion surface smoothness in thermoplastic vulcanizates |
US20080081874A1 (en) * | 2006-09-29 | 2008-04-03 | Kim Balfour | Poly(arylene ether) composition, method, and article |
US20080081879A1 (en) * | 2006-09-29 | 2008-04-03 | Kim Balfour | Crosslinked block copolymer composition and method |
US7615589B2 (en) | 2007-02-02 | 2009-11-10 | Exxonmobil Chemical Patents Inc. | Properties of peroxide-cured elastomer compositions |
WO2012080159A1 (en) * | 2010-12-14 | 2012-06-21 | Styron Europe Gmbh | Improved elastomer formulations |
US9353240B2 (en) | 2010-12-14 | 2016-05-31 | Molecular Rebar Design, Llc | Elastomer formulations comprising discrete carbon nanotube fibers |
US9422413B1 (en) | 2010-12-14 | 2016-08-23 | Molecular Rebar Design, Llc | Elastomer formulations comprising discrete carbon nanotube fibers |
US9493626B1 (en) | 2010-12-14 | 2016-11-15 | Molecular Rebar Design, Llc | Dispersions comprising discrete carbon nanotube fibers |
US9636649B2 (en) | 2010-12-14 | 2017-05-02 | Molecular Rebar Design, Llc | Dispersions comprising discrete carbon nanotube fibers |
CN109843998A (zh) * | 2016-09-14 | 2019-06-04 | 新橡胶科技控股有限公司 | 来源于脱硫橡胶的热塑性弹性体 |
EP3512908A4 (de) * | 2016-09-14 | 2020-10-14 | New Rubber Technologies Holdings, Inc. | Aus entvulkanisiertem kautschuk stammende thermoplastische elastomere |
US11292902B2 (en) | 2018-01-31 | 2022-04-05 | Mcpp Innovation Llc | Modified elastomer composition, crosslinked elastomer composition, and molded article thereof |
Also Published As
Publication number | Publication date |
---|---|
EP1470187A1 (de) | 2004-10-27 |
US7572858B2 (en) | 2009-08-11 |
EP1470187B1 (de) | 2008-04-30 |
DE60320635D1 (de) | 2008-06-12 |
ATE393797T1 (de) | 2008-05-15 |
JP2005516098A (ja) | 2005-06-02 |
DE60320635T2 (de) | 2009-06-04 |
WO2003064523A1 (en) | 2003-08-07 |
JP4361373B2 (ja) | 2009-11-11 |
US20050043484A1 (en) | 2005-02-24 |
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