WO1998029509A1 - Blends of polyolefin and poly(ethylene oxide) and process for making the blends - Google Patents
Blends of polyolefin and poly(ethylene oxide) and process for making the blends Download PDFInfo
- Publication number
- WO1998029509A1 WO1998029509A1 PCT/US1997/024246 US9724246W WO9829509A1 WO 1998029509 A1 WO1998029509 A1 WO 1998029509A1 US 9724246 W US9724246 W US 9724246W WO 9829509 A1 WO9829509 A1 WO 9829509A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight percent
- ethylene oxide
- polyolefin
- poly
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/06—Polyethene
-
- 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
- C08L23/12—Polypropene
-
- 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
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/24—Graft or block copolymers according to groups C08L51/00, C08L53/00 or C08L55/02; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/931—Blend of stated incompatibility
Definitions
- the present invention relates to blends of polyolefin and poly(ethylene oxide) and a method of making the blends. More particularly, the invention relates to blends having up to about 85 weight percent of a modified polyethylene or modified polypropylene and a modified poly(ethylene oxide) and a method of making the modified polyolefin and modified poly(ethylene oxide) blend using a single step reactive extruder.
- Personal care products such as, diapers, sanitary napkins, adult incontinence garments, and the like are generally constructed from a number of different components and materials.
- Such articles typically have a portion, usually the backing layer, liner, or baffle constructed of a liquid repellent film material.
- This repellent material is appropriately constructed to minimize or prevent the exudation of the absorbed liquid from the article and to obtain greater utilization of the absorbent capacity of the product.
- the liquid repellent film commonly used includes plastic materials such as polyethylene films and the like.
- the packaging in which the disposable article is distributed is also made from a water resistant material. Water resistivity is necessary to prevent the degradation of the packaging from environmental conditions and to protect the disposable articles therein.
- this packaging may be safely stored with other refuse for commercial disposal, and especially in the case of individual packaging of the products, it is often more convenient to dispose of the packaging in the toilet with the discarded disposable article.
- plugging of the drains to the toilet typically results.
- hydrophilic materials to be treated with a hydrophobic material to impart the desired water resistant properties to the material.
- the second method has been to modify a water resistant polymer.
- One of the more useful ways of modifying polymers involves blending them with other polymers of different structures and properties.
- polymer blend combinations are thermodynamically miscible and exhibit physical and mechanical compatibility.
- Phase separated blends can in some cases exhibit physical and mechanical compatibility where the polymer compositions are similar, for example, polyolefin blended with other similar polyolefins, or where interfacial agents are added to improve the compatibility at the interface between the constituents of the polymer blend.
- Polymer blends of polyolefins and poly(ethylene oxide) are melt processible but exhibit very poor mechanical compatibility. This poor mechanical compatibility is manifested in the mechanical property profile of the blends relative to the properties of the unblended constituents.
- one aspect of the present invention provides for a modified polyolefin and modified poly(ethylene oxide) blend composition.
- the blend composition is composed of from about 1 weight percent to about 85 weight percent of a modified polyolefin and from about 99 weight percent to about 15 weight percent of a modified poly(ethylene oxide).
- the modified polyolefin and modified poly(ethylene oxide) have grafted thereto from about 1 weight percent to about 30 weight percent, based on the weight of the polyolefin and poly(ethylene oxide), of a monomer.
- Another aspect of the invention provides for a method of making the modified polyolefin and modified poly(ethylene oxide) blend composition.
- the method provides a single pass, melt reactive extrusion modification of the polyolefin and poly(ethylene oxide).
- This single step process affords significant advantages over a two step process where the polyolefin is first modified by grafting a monomer onto the polyolefin backbone which is then re-extruded with the poly(ethylene oxide).
- a few of the advantages include cost savings, reduced polymer degradation and greater uniformity in the final product.
- the method of preparing the blend of modified polyolefin and modified poly(ethylene oxide) using a single pass, melt reactive extruder comprises melting the polyolefin and poly(ethylene oxide) in the extruder and adding to the polyolefin and poly(ethylene oxide) blend a monomer and a sufficient amount of a free radical initiator to graft from about 1 weight percent to about 100 weight percent of the monomer onto the polyolefin and poly(ethylene oxide).
- Another object of the invention is to provide a method of making a modified polyolefin and modified poly(ethylene oxide) blend composition using a single pass reactive extruder.
- reactive extrusion is the use of chemical reactions during polymer extrusion to form desired products. Free radical initiator, crosslinking agents, and other reactive additives can be injected into the extruder to cause such reactions.
- one aspect of the invention is for a composition of matter comprising a polymer blend having from about 1 weight percent to about 85 weight percent of a modified polyolefin and from about 99 weight percent to about 15 weight percent of a modified poly(ethylene oxide).
- the blend comprises from about 30 weight percent to about 85 weight percent of a modified polyolefin and from about 70 weight percent to about 15 weight percent of modified poly(ethylene oxide). More preferably, the blend comprises from about 55 weight percent to about 85 weight percent of a modified polyolefin and from about 45 weight percent to about 15 weight percent of modified poly(ethylene oxide).
- the amount of monomer added to the blend of polyolefin and poly(ethylene oxide) is from about 1 weight percent to about 30 weight percent, preferably, from about 1 weight percent to about 20 weight percent and more preferably, from about 1 weight percent to about 10 weight percent wherein all such ranges are based on the total weight of the polyolefin and poly(ethylene oxide).
- the saturated ethylene polymers useful in the practice of this invention are homopolymers or copolymers of ethylene and polypropylene and are essentially linear in structure.
- the term "saturated” refers to polymers which are fully saturated, but also includes polymers containing up to about 5% unsaturation.
- the homopolymers of ethylene include those prepared under either low pressure, i.e., linear low density or high density polyethylene, or high pressure, i.e., branched or low density polyethylene.
- the high density polyethylenes are generally characterized by a density that is about equal to or greater than 0.94 grams per cubic centimeter (g/cc).
- the high density polyethylenes useful as the base resin in the present invention have a density ranging from about 0.94 g/cc to about 0.97 g/cc.
- the polyethylenes can have a melt index, as measured at 2.16 kg and 190°O, ranging from about 0.005 decigrams per minute (dg/min) to 100 dg/min.
- the polyethylene has a melt index of 0.01 dg/min to about 50 dg/min and more desirably of 0.05 dg/min to about 25 dg/min.
- mixtures of polyethylene can be used as the base resin in producing the graft copolymer compositions, and such mixtures can have a melt index greater than 0.005 dg/min to less than about 100 dg/min.
- the low density polyethylene has a density of less than 0.94 g/cc and are usually in the range of 0.91 g/cc to about 0.93 g/cc.
- the low density polyethylene polymer has a melt index ranging from about 0.05 dg/min to about 100 dg/min and desirably from 0.05 dg/min to about 20 dg/min.
- Ultra low density polyethylene can be used in accordance with the present invention. Generally, ultra low density polyethylene has a density of less than 0.90g/cc.
- polypropylene has a semi-crystalline structure having a molecular weight of about 40,000 or more, a density of about 0.90 g/cc, a melting point of 168 to 171°C for isotactic polypropylene and a tensile strength of 5000 psi.
- Polypropylene can also have other tacticities including syndiotactic and atactic.
- the above polyolefins can also be manufactured by using the well known multiple-site Ziegler-Natta catalysts or the more recent single-site metallocene catalysts.
- the metallocene catalyzed polyolefins have better controlled polymer microstructures than polyolefins manufactured using Ziegler-Natta catalysts, including narrower molecular weight distribution, well controlled chemical composition distribution, co- monomer sequence length distribution, and stereoregularity.
- Metallocene catalysts are known to polymerize propylene into atactic, isotactic, syndiotactic, isotactic-atactic steroblock copolymer.
- Copolymers of ethylene which can be useful in the present invention may include copolymers of ethylene with one or more additional polymerizable, unsaturated monomers.
- copolymers include, but are not limited to, copolymers of ethylene and alpha olefins (such as propylene, butene, hexene or octene) including linear low density polyethylene, copolymers of ethylene and vinyl esters of linear or branched carboxylic acids having 1-24 carbon atoms such as ethylene-vinyl acetate copolymers, and copolymers of ethylene and acrylic or methacrylic esters of linear, branched or cyclic alkanols having 1-28 carbon atoms. Examples of these latter copolymers include ethylene-alkyl (meth)acrylate copolymers, such as ethylene-methyl acrylate copolymers.
- the free radical initiators useful in the practice of this invention include acyl peroxides such as benzoyi peroxide; dialkyi; diaryl; or aralkyi peroxides such as di-t-butyl peroxide; dicumyl peroxide; cumyl butyl peroxide; 1 ,1 -di-t-butyl peroxy-3,5,5- trimethylcyclohexane; 2,5-dimethyl-2,5-di(t-butylperoxy) hexane; 2,5-dimethyl-2,5-bis (t- butylperoxy) hexyne-3 and bis(a-t-butyl peroxyisopropylbenzene); peroxyesters such as t-butyl peroxypivalate; t-butyl peroctoate; t-butyl perbenzoate; 2,5-dimethylhexyl-2,5- di(perbenzoate); t-butyl di(perphthal
- Poly(ethylene oxide) polymers suitable for the present invention can have a molecular weight ranging from 100,000 to 8,000,000.
- Poly(ethylene oxide) is available from Union Carbide Corporation under the trade name of POLYOX ® .
- poly(ethylene oxide) is a dry free flowing white powder having a crystalline melting point in the order of about 65°C, above which poly(ethylene oxide) resin becomes thermoplastic and can be formed by molding, extrusion and other methods known in the art.
- the method of making the polymer blends includes melt blending the desired weight ratios of a mixture of the polyolefin, poly(ethylene oxide), the monomer and a free radical initiator in an extruder and at a reaction temperature where the polyolefin and poly(ethylene oxide) are converted to a molten state. Accordingly, the polyolefin, poly(ethylene oxide), monomer and free radical initiator can be simultaneously added to the extruder before the polymer constituents, i.e., the polyolefin and poly(ethylene oxide) have been melted.
- the preferred monomers used in the present invention are 2- hydroxyethyl methacrylate and polyethylene glycol ethyl ether (meth)acrylate, both are available from Aldrich Chemical Company, Milwaukee, Wisconsin.
- the melt extruder used for melt blending can introduce various constituents into the blend at different locations along the screw length.
- the free radical initiator, crosslinking agents, or other reactive additives can be injected into the blend before or after one or more of the polymer constituents is melted or thoroughly mixed. More preferably, the polyolefin and poly(ethylene oxide) are added at the beginning of the extruder. After melting, the monomer is added to melted polymers and further down the extruder barrel, the free radical initiator is fed to the melt blend.
- the scope of the invention would include simultaneously adding the monomer and free radical initiator into the molten blend of polyolefin and poly(ethylene oxide). It is important to the method of the invention that the polyolefin and poly(ethylene oxide) be melt blended contemporaneously with or before the addition of the monomer and free radical initiator. Although not to be bound by any theory, it is believed that the monomer, in the presence of the free radical initiator, grafts onto both the polyolefin and poly(ethylene oxide) thereby allowing articles made from the blend of modified polyolefin and modified poly(ethylene oxide) to have a greater water responsiveness. As used herein the term "water responsiveness” refers to a loss of tensile strength or strain-to- break of a wet film relative to the dry film tensile strength or strain-to-break.
- the amount of free radical initiator added to the extruder should be an amount sufficient to graft from about 1 percent to 100 percent of the monomer onto the polyolefin and poly(ethylene oxide). This can range from about 0.1 weight percent to about 10 weight percent of initiator. Preferably, the amount of initiator added to the extruder ranges from about 0.1 weight percent to about 5 weight percent wherein all such ranges are based on the amount of monomer added to the melt blend.
- thermoplastic article made from the modified polyolefin and modified poly(ethylene oxide) blend described above is water responsive.
- the present invention is illustrated in greater detail by the specific examples presented below. It is to be understood that these examples are illustrative embodiments and are not intended to be limiting of the invention, but rather are to be construed broadly within the scope and content of the appended claims.
- Comparative Example A is a physical blend of the polymer resins.
- the blends of Comparative Examples B-D were prepared by a two-step process. In the first step the polyethylene was modified by grafting a monomer thereto. The method of making the modified polyethylene is described in greater detail in the copending U.S. patent application having U.S. Serial Number 08/733,410 filed on October 18, 1996 the entire disclosure of which is incorporated herein by reference.
- the modified polyolefin is blended with the poly(ethylene oxide). Select properties of these materials are in Table 1 below. Examples 1-4, 5-8 and 9-10 were made in accordance with the present invention. Select properties of these materials are in Tables 2, 3 and 4 respectively.
- COMPARATIVE EXAMPLE A A 60/40 weight percent resin blend of low density polyethylene having a melt index of 2.3 decigrams per minute (dg/min) and a density of 0.917 grams per cubic centimeter (g/cc) (Dow 5031 ; available from Dow Chemical Company, Midland, Mich.) and poly(ethylene oxide) having a molecular weight of 200,000 g/mol. (POLYOX ® WSRN-80 available from Union Carbide Corp.) were fed to a Haake counter-rotating twin screw extruder at a rate of 5 pounds per hour (Ib/hr). The extruder had a length of 300 millimeters.
- Each conical screw had 30 millimeters diameter at the feed port and a diameter of 20 millimeters at the die.
- the extruder had four heating zones set at 1 0, 180, 180 and 190 degrees Centigrade (C).
- the screw speed of the extruder was 150 rpm.
- COMPARATIVE EXAMPLES B-D For Comparative Examples B-D the low density polyethylene, Dow 5031, was modified by grafting thereto polyethylene glycol methacrylate (PEG-MA; available from Aldrich Chemical Company, Milwaukee, WI).
- PEG-MA polyethylene glycol methacrylate
- the feed to the extruder comprised contemporaneously adding, at the extruder feed throat, 5 Ib/hr of polyethylene and the specified amounts of PEG-MA and free radical initiator ((2, 5-dimethyl-2, 5-di(t-butylperoxy) hexane, supplied by Atochem, 2000 Market St. Philadelphia, PA under the tradename of LUPERSOL 101).
- a 60/40 blend was prepared following the method of Comparative Example A above, except the modified polyethylene of each example was substituted for the unmodified polyethylene.
- the resulting products had the characteristics indicated in Table 1.
- Film processing of the blends was performed using the Haake extruder as described above with the following modifications.
- the extruder included a 4 inch slit die at a temperature of 195 degrees C.
- the screw speed was at 30 rpm.
- a chilled wind-up roll was used to collect the film.
- the chilled roll was operated at a speed sufficient to form a film having a thickness of about 4 mils (0.004 of an inch) and was maintained at a temperature of about 15-20 degrees C.
- Dry tensile tests were performed on a Sintech 1/D tensile tester available from MTS Systems Corp., Machesny Park, IL.
- the film was cut into a type V dogbone shape in accordance with ASTM D638.
- the test was performed with a grip separation of 30 millimeters and a crosshead speed of 4 millimeters/second.
- the 60/40 weight percent resin blend of low density polyethylene (Dow 5031) and poly(ethylene oxide) (WSRN-80) was fed to the Haake counter-rotating twin screw extruder at a rate of 5 Ib/hr. Contemporaneously with the polymer feed to the extruder, specified amounts of the monomer, PEG-MA, and free radical initiator (LUPERSOL 101) were added at the feed throat.
- the extruder had four heating zones set at 170, 180, 180 and 190 degrees C.
- the screw speed of the extruder was 150 rpm.
- Example 1 the PEG-MA feed rate was 0.125 Ib/hr and the initiator rate was 0.0125 Ib/hr.
- Example 2 the PEG-MA feed rate was 0.25 Ib/hr and the initiator rate was 0.025 Ib/hr.
- Example 3 the PEG-MA feed rate was 0.5 Ib/hr and the initiator rate was 0.025 Ib/hr.
- Example 4 the PEG-MA feed rate was 0.75 Ib/hr and the initiator rate was 0.0375 Ib/hr.
- the amount of monomer grafted to polyethylene was 0.65 weight percent, 1.03 weight percent, 0.51 weight percent and 1.13 weight percent, respectively.
- the weight percent of monomer grafted to the polyethylene was determined by FT-IR and elemental oxygen content as described in copending U.S. patent application 08/733,410 filed October 18, 1996 the entire disclosure of which is inco ⁇ orated herein by reference.
- the amount of monomer grafted to the poly(ethylene oxide) was determined to be 14.9 weight percent by proton NMR spectroscopy.
- the 60/40 weight percent resin blend of low density polyethylene (Dow 5031) and poly(ethylene oxide) (WSRN-80) was fed to the Haake counter-rotating twin screw extruder at a rate of 5 Ib/hr. Contemporaneously with the polymer feed to the extruder, specified amounts of a monomer, 2-hydroxy ethyl methacrylate, and free radical initiator (LUPERSOL 101) were added at the feed throat.
- the extruder had four heating zones set at 170, 180, 180 and 190 degrees C.
- the screw speed of the extruder was 150 ⁇ m.
- Example 5 the 2-hydroxyethyl methacrylate feed rate was 0.125 Ib/hr and the initiator rate was 0.0125 Ib/hr.
- Example 6 the 2- hydroxyethyl methacrylate feed rate was 0.25 Ib/hr and the initiator rate was 0.025 Ib/hr.
- Example 7 the 2- hydroxyethyl methacrylate feed rate was 0.5 Ib/hr and the initiator rate was 0.025 Ib/hr.
- Example 8 the 2- hydroxyethyl methacrylate feed rate was 0.75 Ib/hr and the initiator rate was 0.0375 Ib/hr.
- a 30/70 weight percent resin blend of low density polyethylene (Dow 5031) and poly(ethylene oxide) (WSRN-80) was fed to the Haake counter-rotating twin screw extruder at a rate of 5 Ib/hr. Contemporaneously with the polymer feed to the extruder, specified amounts of a monomer, polyethylene glycol ethyl ether (meth)acrylate, and free radical initiator (LUPERSOL 101) were added at the feed throat.
- the extruder had four heating zones set at 170, 180, 180 and 190 degrees C.
- the screw speed of the extruder was 150 ⁇ m.
- Example 9 the polyethylene glycol ethyl ether (meth)acrylate feed rate was 0.25 Ib/hr and the initiator rate was 0.05 Ib/hr.
- EXAMPLE 10 the polyethylene glycol ethyl ether (meth)acrylate feed rate was 0.25 Ib/hr and the initiator rate was 0.05 Ib/hr.
- a 80/20 weight percent resin blend of low density polyethylene (Dow 5031) and poly(ethylene oxide) (WSRN-80) was fed to the Haake counter-rotating twin screw extruder at a rate of 5 Ib/hr. Contemporaneously with the polymer feed to the extruder, specified amounts of a monomer, polyethylene glycol ethyl ether (meth)acrylate, and free radical initiator (LUPERSOL 101) were added at the feed throat.
- the extruder had four heating zones set at 170, 180, 180 and 190 degrees Centigrade (C).
- the screw speed of the extruder was 150 ⁇ m.
- Example 10 the polyethylene glycol ethyl ether (meth)acrylate feed rate was 0.25 Ib/hr (5 weight percent addition) and the initiator rate was 0.05 Ib/hr.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002275702A CA2275702A1 (en) | 1996-12-31 | 1997-12-19 | Blends of polyolefin and poly(ethylene oxide) and process for making the blends |
| DE69720523T DE69720523T2 (de) | 1996-12-31 | 1997-12-19 | Polyolefin-polyethylenoxid-mischungen und verfahren zu deren herstellung |
| IL13056897A IL130568A (en) | 1996-12-31 | 1997-12-19 | Mixtures of polyolefin and poly (ethyl oxide) and process for preparing the mixtures |
| EP97953574A EP0951509B1 (en) | 1996-12-31 | 1997-12-19 | Blends of polyolefin and poly(ethylene oxide) and process for making the blends |
| JP53034398A JP2001507745A (ja) | 1996-12-31 | 1997-12-19 | ポリオレフィンとポリ(エチレンオキシド)とのブレンド及び該ブレンドの製造方法 |
| KR10-1999-7005915A KR100523502B1 (ko) | 1996-12-31 | 1997-12-19 | 폴리올레핀과 폴리(에틸렌 옥시드)의 배합물 및 그의 제조 방법 |
| AU57293/98A AU729432B2 (en) | 1996-12-31 | 1997-12-19 | Blends of polyolefin and poly(ethylene oxide) and process for making the blends |
| BR9713641-7A BR9713641A (pt) | 1996-12-31 | 1997-12-19 | Misturas de poliolefinas e poli (óxidos de etileno) e processo para fabricação das misturas |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/777,226 | 1996-12-31 | ||
| US08/777,226 US5700872A (en) | 1996-12-31 | 1996-12-31 | Process for making blends of polyolefin and poly(ethylene oxide) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1998029509A1 true WO1998029509A1 (en) | 1998-07-09 |
Family
ID=25109646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/024246 Ceased WO1998029509A1 (en) | 1996-12-31 | 1997-12-19 | Blends of polyolefin and poly(ethylene oxide) and process for making the blends |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5700872A (enExample) |
| EP (1) | EP0951509B1 (enExample) |
| JP (1) | JP2001507745A (enExample) |
| KR (1) | KR100523502B1 (enExample) |
| CN (1) | CN1222575C (enExample) |
| AU (1) | AU729432B2 (enExample) |
| BR (1) | BR9713641A (enExample) |
| CA (1) | CA2275702A1 (enExample) |
| DE (1) | DE69720523T2 (enExample) |
| IL (1) | IL130568A (enExample) |
| WO (1) | WO1998029509A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5916969A (en) * | 1996-11-22 | 1999-06-29 | Kimberly-Clark Corporation | Article and composition of matter made from polyolefins and PEO blend and method of making the same |
| US6255386B1 (en) | 1996-12-31 | 2001-07-03 | Kimberly-Clark Worldwide, Inc. | Blends of polyolefin and poly(ethylene oxide) and process for making the blends |
| US6111014A (en) * | 1996-12-31 | 2000-08-29 | Kimberly-Clark Worldwide, Inc. | Film of monomer-grafted polyolefin and poly(ethylene oxide) |
| US5912076A (en) | 1996-12-31 | 1999-06-15 | Kimberly-Clark Worldwide, Inc. | Blends of polyethylene and peo having inverse phase morphology and method of making the blends |
| US6100330A (en) * | 1996-12-31 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Water-degradable film of monomer grafted to polyolefin and poly(ethylene oxide) |
| US6063866A (en) * | 1996-12-31 | 2000-05-16 | Kimberly-Clark Worldwide, Inc. | Blends of polyolefin and poly(ethylene oxide) and process for making the blends |
| US5976694A (en) | 1997-10-03 | 1999-11-02 | Kimberly-Clark Worldwide, Inc. | Water-sensitive compositions for improved processability |
| US6172177B1 (en) * | 1997-12-31 | 2001-01-09 | Kimberly-Clark Worldwide, Inc. | Grafted poly(ethylene oxide) compositions |
| US6090472A (en) * | 1997-12-31 | 2000-07-18 | Kimberly-Clark Worldwide, Inc. | Nonwoven, porous fabric produced from polymer composite materials |
| US6071451A (en) * | 1997-12-31 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Process for making a nonwoven, porous fabric from polymer composite materials |
| US6372850B2 (en) | 1997-12-31 | 2002-04-16 | Kimberly-Clark Worldwide, Inc. | Melt processable poly (ethylene oxide) fibers |
| AU2022599A (en) * | 1997-12-31 | 1999-07-19 | Kimberly-Clark Worldwide, Inc. | Method of reducing molecular weights and polydispersity indices of polymers of ethylene oxide |
| WO1999034042A1 (en) | 1997-12-31 | 1999-07-08 | Kimberley-Clark Worldwide, Inc. | Flushable fiber compositions comprising modified polypropylene and modified poly(ethylene oxide) and process for making the same |
| WO1999033922A1 (en) * | 1997-12-31 | 1999-07-08 | Kimberly-Clark Worldwide, Inc. | Method of modifying poly(ethylene oxide) |
| US6117947A (en) * | 1997-12-31 | 2000-09-12 | Kimberly-Clark Worldwide, Inc. | Method of modifying poly(ethylene oxide) |
| AU2208299A (en) * | 1997-12-31 | 1999-07-19 | Kimberly-Clark Worldwide, Inc. | Flushable poly(ethylene oxide) films with balanced mechanical properties |
| US6350518B1 (en) | 1998-06-01 | 2002-02-26 | Kimberly-Clark Worldwide, Inc. | Methods of making blend compositions of an unmodified poly vinyl alcohol and a thermoplastic elastomer |
| US6410823B1 (en) * | 1998-06-30 | 2002-06-25 | Kimberly-Clark Worldwide, Inc. | Apertured film covers with localized wettability and method for making the same |
| US6369293B1 (en) | 1998-11-04 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Absorbent composition including an uncrosslinked polymer |
| KR20010099995A (ko) * | 1998-12-29 | 2001-11-09 | 로날드 디. 맥크레이 | 열-활성화 접착제 |
| AR022140A1 (es) | 1998-12-31 | 2002-09-04 | Kimberly Clark Co | Una composicion de materia, una pelicula y un articulo que comprenden dicha composicion y el proceso para hacer dicha composicion |
| AU4681899A (en) * | 1999-06-07 | 2000-12-28 | Kimberly-Clark Worldwide, Inc. | Inverse phase blends of poly(ethylene oxide) and polyolefin and reactive extrusion method of making inverse phase blends |
| AU5897000A (en) * | 1999-06-29 | 2001-01-31 | Kimberly-Clark Worldwide, Inc. | Compositions comprising a blend of poly(ethylene oxide) and grafted polyolefin and method of making the same |
| US6580015B2 (en) * | 1999-09-14 | 2003-06-17 | Kimberly-Clark Worldwide, Inc. | Absorbent composition including an uncrosslinked polymer |
| US6444761B1 (en) | 1999-12-28 | 2002-09-03 | Kimberly-Clark Worldwide, Inc. | Water-soluble adhesive compositions |
| US6576576B1 (en) | 1999-12-29 | 2003-06-10 | Kimberly-Clark Worldwide, Inc. | Multicomponent fibers |
| US6610793B1 (en) | 2000-05-26 | 2003-08-26 | Kimberly-Clark Worldwide, Inc. | Modified poly(ethylene oxide), method of making same and articles using same |
| US6790519B1 (en) | 2000-05-26 | 2004-09-14 | Kimberly-Clark Worldwide, Inc. | Moisture-induced poly(ethylene oxide) gel, method of making same and articles using same |
| US6767961B1 (en) | 2000-06-19 | 2004-07-27 | Kimberly-Clark Worldwide, Inc. | Blends of poly (vinyl alcohol) and poly (ethylene oxide) and articles made therewith |
| US6958371B1 (en) | 2000-06-19 | 2005-10-25 | Kimberly-Clark Worldwide, Inc. | Method of making blends of poly(vinyl alcohol) and poly(ethylene oxide) |
| US6403706B1 (en) | 2000-12-28 | 2002-06-11 | Kimberly-Clark Worldwide, Inc. | Methods of making polymer/dispersed modifier compositions |
| US6607819B2 (en) | 2000-12-28 | 2003-08-19 | Kimberly-Clark Worldwide, Inc. | Polymer/dispersed modifier compositions |
| US6500897B2 (en) | 2000-12-29 | 2002-12-31 | Kimberly-Clark Worldwide, Inc. | Modified biodegradable compositions and a reactive-extrusion process to make the same |
| US6552124B2 (en) | 2000-12-29 | 2003-04-22 | Kimberly-Clark Worldwide, Inc. | Method of making a polymer blend composition by reactive extrusion |
| US6579934B1 (en) | 2000-12-29 | 2003-06-17 | Kimberly-Clark Worldwide, Inc. | Reactive extrusion process for making modifiied biodegradable compositions |
| US7053151B2 (en) | 2000-12-29 | 2006-05-30 | Kimberly-Clark Worldwide, Inc. | Grafted biodegradable polymer blend compositions |
| US6835708B2 (en) | 2001-03-07 | 2004-12-28 | Nippon Shokubai Co., Ltd. | Graft polymer composition and its production process and uses |
| US6890989B2 (en) | 2001-03-12 | 2005-05-10 | Kimberly-Clark Worldwide, Inc. | Water-responsive biodegradable polymer compositions and method of making same |
| US6509419B1 (en) * | 2001-07-12 | 2003-01-21 | Kimberly-Clark Worldwide, Inc. | Chemically modified polyethylene oxide compositions with improved environmental stability |
| US6515075B1 (en) | 2001-07-12 | 2003-02-04 | Kimberly-Clark Worldwide, Inc. | Films, fibers and articles of chemically modified polyethylene oxide compositions with improved environmental stability and method of making same |
| KR20030026459A (ko) * | 2001-09-25 | 2003-04-03 | 현대자동차주식회사 | 차량 범퍼 도장방법 |
| BR112015011656A2 (pt) * | 2012-12-04 | 2017-07-11 | Braskem Sa | método de compatibilização de blendas de polipropileno, blenda de polipropileno preparada, uso de uma blenda de polipropileno, produto de material processado, e, agente iniciador de compatibilização de blenda de polipropileno |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666737A (en) * | 1970-08-06 | 1972-05-30 | Goodyear Tire & Rubber | Method and process of preparing improved polyethers |
| US4080405A (en) * | 1975-12-23 | 1978-03-21 | Ato Chimie | Process for chemical modification of polyolefins to improve their wettability |
| US5209849A (en) * | 1992-04-24 | 1993-05-11 | Gelman Sciences Inc. | Hydrophilic microporous polyolefin membrane |
| US5367003A (en) * | 1991-04-23 | 1994-11-22 | Petcavich Robert J | Disposable degradable recyclable plastic articles and synthetic resin blends for making the same |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3323978A (en) * | 1963-05-09 | 1967-06-06 | Phillips Petroleum Co | Artificial textile fibres and their production |
| US3539666A (en) * | 1968-06-18 | 1970-11-10 | Grace W R & Co | Method for preparing a nonwoven fabriclike member |
| FR2045934A1 (enExample) * | 1969-06-09 | 1971-03-05 | Union Carbide Corp | |
| US3717541A (en) * | 1970-06-30 | 1973-02-20 | Grace W R & Co | Non-woven fabric-like member |
| US3954928A (en) * | 1970-07-28 | 1976-05-04 | Teijin Ltd. | Process for making sheet-formed reticulated fibrous structures |
| BE789277A (fr) * | 1971-09-27 | 1973-03-26 | Union Carbide Corp | Composition de polymere d'ethylene degradable sous l'action desintemperies |
| JPS521740B2 (enExample) * | 1973-04-06 | 1977-01-18 | ||
| US4018729A (en) * | 1974-10-01 | 1977-04-19 | Union Carbide Corporation | Shaped article for conditioning hair a blend of water-soluble and water-insoluble polymers with interpenetrating networks |
| US4186233A (en) * | 1978-03-27 | 1980-01-29 | The Dow Chemical Company | Disposable composite insensitive to surface moisture but disintegratable in aqueous liquid |
| US4528334A (en) * | 1978-11-24 | 1985-07-09 | Union Carbide Corporation | Carboxylated poly(oxyalkylenes) |
| US4624051A (en) * | 1984-12-07 | 1986-11-25 | The Gillette Company | Shaving unit |
| JPS61272217A (ja) * | 1985-05-29 | 1986-12-02 | Ube Ind Ltd | ポリオレフイン樹脂組成物 |
| US4868222A (en) * | 1985-06-10 | 1989-09-19 | The Dow Chemical Company | Preparation of asymmetric membranes by the solvent extraction of polymer components from polymer blends |
| US5095619A (en) * | 1990-09-28 | 1992-03-17 | The Gillette Company | Shaving system |
| CA2050021C (en) * | 1990-10-16 | 2002-07-02 | Kimberly-Clark Worldwide, Inc. | Environmentally friendly polymeric web compositions |
| EP0503909A1 (en) * | 1991-03-14 | 1992-09-16 | Chevron Research And Technology Company | Substantially non-crosslinked maleic anhydride-modified ethylene polymers and process for preparing same |
| AU666592B2 (en) * | 1991-04-23 | 1996-02-15 | Robert J. Petcavich | Disposable degradable recyclable plastic articles and synthetic resin blends for making the same |
| NZ242597A (en) * | 1991-05-14 | 1995-07-26 | Grace W R & Co | Co-extruded water soluble laminated polymeric film and methods of extruding it |
| HK1006423A1 (en) * | 1991-06-26 | 1999-02-26 | The Procter & Gamble Company | Disposable absorbent articles with biodegradable backsheets |
| US5571878A (en) * | 1991-09-24 | 1996-11-05 | Chevron Chemical Company | Ethylene-alkyl acrylate copolymers and derivatives having improved melt-point temperatures and adhesive strength and processes for preparing same |
| EP0555197A3 (en) * | 1992-01-29 | 1993-11-18 | Monsanto Co | Antistatic agent for thermoplastic polymers |
| KR100262356B1 (ko) * | 1992-06-26 | 2000-09-01 | 데이비드 엠 모이어 | 생분해성 액체 불투과성 다층 필름 조성물 |
| CA2138121C (en) * | 1992-06-26 | 1999-02-23 | Andrew Julian Wnuk | Biodegradable, liquid impervious monolayer film compositions |
| US5369168A (en) * | 1992-08-03 | 1994-11-29 | Air Products And Chemicals, Inc. | Reactive melt extrusion grafting of thermoplastic polyvinyl alcohol/polyolefin blends |
| US5468259A (en) * | 1992-12-07 | 1995-11-21 | Sheth; Paresh J. | Dyeable polyolefin compositions and dyeing polyolefin compositions |
| DE4312753A1 (de) * | 1993-04-20 | 1994-10-27 | Basf Ag | Verwendung von Polyacetalen zur Herstellung von kompostierbaren Formkörpern, als Beschichtungsmittel und als Klebstoff |
| US5395308A (en) * | 1993-09-24 | 1995-03-07 | Kimberly-Clark Corporation | Thermoplastic applicator exhibiting accelerated breakup when immersed in water |
| US5415905A (en) * | 1993-09-29 | 1995-05-16 | Exxon Chemical Patents Inc. | Dispersible film |
| WO1995011929A1 (en) * | 1993-10-27 | 1995-05-04 | Chevron Chemical Company | Low-haze ionomers of copolymers of alpha-olefins, carboxylic acid esters, and optional comonomers, and processes for making and acidifying these ionomers |
| CA2128483C (en) * | 1993-12-16 | 2006-12-12 | Richard Swee-Chye Yeo | Flushable compositions |
| US5498785A (en) * | 1994-01-14 | 1996-03-12 | Chevron Chemical Company | Continuous process for the aminolysis of ethylene copolymers |
| SG49096A1 (en) * | 1994-01-28 | 1998-05-18 | Procter & Gamble | Biodegradable 3-polyhydtoxybuyrate/3- polyhydroxyhexanoate copolymer films |
| ZA95627B (en) * | 1994-01-28 | 1995-10-05 | Procter & Gamble | Biodegradable copolymers and plastic articles comprising biodegradable copolymers |
| ID23491A (id) * | 1994-01-28 | 1995-09-07 | Procter & Gamble | Kopolimer-kopolimer yang dapat dibiodegradasi dan baha-bahan plastik yang terdiri dari kopolimer-kopolimer yang dapat dibiodegradasi |
| BR9506664A (pt) * | 1994-01-28 | 1997-09-16 | Procter & Gamble | Copolímeros biodegradâveis e artigos plásticos compreendendo copolímeros biodegradâveis de 3-hidroxihexanoato |
| HUT78003A (hu) * | 1994-02-28 | 1999-05-28 | The Procter & Gamble Co. | Keverési eljárások biológiailag lebontható rostszálacskák, ezeket tartalmazó szövés nélküli anyagok és a szövés nélküli anyagokat tartalmazó cikkek előállítására |
| SG44660A1 (en) * | 1994-02-28 | 1997-12-19 | Procter & Gamble | Spray processes using a gaseous flow for preparing biodegradable fibrils nonwoven fabrics comprising biodegradable fibrils and articles comprising such nonwoven fabrics |
| US5549791A (en) * | 1994-06-15 | 1996-08-27 | The Procter & Gamble Company | Individualized cellulosic fibers crosslinked with polyacrylic acid polymers |
| US5472518A (en) * | 1994-12-30 | 1995-12-05 | Minnesota Mining And Manufacturing Company | Method of disposal for dispersible compositions and articles |
| US5759569A (en) * | 1995-01-10 | 1998-06-02 | The Procter & Gamble Company | Biodegradable articles made from certain trans-polymers and blends thereof with other biodegradable components |
| GB2295553B (en) * | 1995-02-09 | 1997-05-21 | Ecoprogress Ltd | A water dispersible bodily liquid absorbent composite |
-
1996
- 1996-12-31 US US08/777,226 patent/US5700872A/en not_active Expired - Lifetime
-
1997
- 1997-05-16 US US08/857,411 patent/US5807930A/en not_active Expired - Lifetime
- 1997-12-19 WO PCT/US1997/024246 patent/WO1998029509A1/en not_active Ceased
- 1997-12-19 JP JP53034398A patent/JP2001507745A/ja not_active Abandoned
- 1997-12-19 BR BR9713641-7A patent/BR9713641A/pt not_active IP Right Cessation
- 1997-12-19 AU AU57293/98A patent/AU729432B2/en not_active Ceased
- 1997-12-19 CA CA002275702A patent/CA2275702A1/en not_active Abandoned
- 1997-12-19 KR KR10-1999-7005915A patent/KR100523502B1/ko not_active Expired - Fee Related
- 1997-12-19 CN CNB971819351A patent/CN1222575C/zh not_active Expired - Fee Related
- 1997-12-19 IL IL13056897A patent/IL130568A/en not_active IP Right Cessation
- 1997-12-19 DE DE69720523T patent/DE69720523T2/de not_active Expired - Lifetime
- 1997-12-19 EP EP97953574A patent/EP0951509B1/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666737A (en) * | 1970-08-06 | 1972-05-30 | Goodyear Tire & Rubber | Method and process of preparing improved polyethers |
| US4080405A (en) * | 1975-12-23 | 1978-03-21 | Ato Chimie | Process for chemical modification of polyolefins to improve their wettability |
| US5367003A (en) * | 1991-04-23 | 1994-11-22 | Petcavich Robert J | Disposable degradable recyclable plastic articles and synthetic resin blends for making the same |
| US5209849A (en) * | 1992-04-24 | 1993-05-11 | Gelman Sciences Inc. | Hydrophilic microporous polyolefin membrane |
Also Published As
| Publication number | Publication date |
|---|---|
| US5700872A (en) | 1997-12-23 |
| DE69720523D1 (de) | 2003-05-08 |
| EP0951509B1 (en) | 2003-04-02 |
| CN1222575C (zh) | 2005-10-12 |
| EP0951509A1 (en) | 1999-10-27 |
| IL130568A (en) | 2001-10-31 |
| IL130568A0 (en) | 2000-06-01 |
| US5807930A (en) | 1998-09-15 |
| DE69720523T2 (de) | 2004-04-29 |
| AU5729398A (en) | 1998-07-31 |
| CN1247550A (zh) | 2000-03-15 |
| KR20000069776A (ko) | 2000-11-25 |
| AU729432B2 (en) | 2001-02-01 |
| BR9713641A (pt) | 2001-09-18 |
| JP2001507745A (ja) | 2001-06-12 |
| KR100523502B1 (ko) | 2005-10-25 |
| CA2275702A1 (en) | 1998-07-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5807930A (en) | Process for making blends of polyolefin and poly(ethylene oxide) | |
| EP0951508B1 (en) | Blends of polyethylene and peo having inverse phase morphology and method of making the blends | |
| US6063866A (en) | Blends of polyolefin and poly(ethylene oxide) and process for making the blends | |
| US6255386B1 (en) | Blends of polyolefin and poly(ethylene oxide) and process for making the blends | |
| WO1998029502A1 (en) | Water-modifiable flushable polyolefin-containing film | |
| US6111014A (en) | Film of monomer-grafted polyolefin and poly(ethylene oxide) | |
| US6100330A (en) | Water-degradable film of monomer grafted to polyolefin and poly(ethylene oxide) | |
| AU732005B2 (en) | Mesh-forming material and method of making the same | |
| MXPA00012673A (en) | Blends of polyolefin and poly(ethylene oxide) and process for making the blends | |
| CZ234799A3 (cs) | Směsi polyolefinu a poly(ethylenoxidu) a způsob jejich přípravy | |
| MXPA01003944A (es) | Mezclas de poliolefina y de poli(oxido de etileno) y proceso para hacer las mezclas. | |
| WO2000075228A1 (en) | Inverse phase blends of poly(ethylene oxide) and polyolefin and reactive extrusion method of making inverse phase blends | |
| MXPA00012369A (en) | Water-modifiable flushable polyolefin-containing film and article made therefrom | |
| MXPA00012368A (en) | Water-modifiable flushable polyolefin-containing film and article made therefrom | |
| MXPA99006201A (en) | Blends of polyethylene and peo having inverse phase morphology and method of making the blends |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WWE | Wipo information: entry into national phase |
Ref document number: 97181935.1 Country of ref document: CN |
|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG UZ VN YU ZW AM AZ BY KG KZ MD RU TJ TM |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW SD SZ UG ZW AT BE CH DE DK ES FI FR GB GR IE IT LU MC |
|
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| ENP | Entry into the national phase |
Ref document number: 2275702 Country of ref document: CA Ref document number: 2275702 Country of ref document: CA Kind code of ref document: A |
|
| WWE | Wipo information: entry into national phase |
Ref document number: PV1999-2347 Country of ref document: CZ |
|
| WWE | Wipo information: entry into national phase |
Ref document number: PA/a/1999/006126 Country of ref document: MX Ref document number: 1019997005915 Country of ref document: KR |
|
| ENP | Entry into the national phase |
Ref document number: 1998 530343 Country of ref document: JP Kind code of ref document: A |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 1997953574 Country of ref document: EP |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 57293/98 Country of ref document: AU |
|
| WWP | Wipo information: published in national office |
Ref document number: 1997953574 Country of ref document: EP |
|
| REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
| WWP | Wipo information: published in national office |
Ref document number: PV1999-2347 Country of ref document: CZ |
|
| WWP | Wipo information: published in national office |
Ref document number: 1019997005915 Country of ref document: KR |
|
| WWG | Wipo information: grant in national office |
Ref document number: 57293/98 Country of ref document: AU |
|
| WWG | Wipo information: grant in national office |
Ref document number: 1997953574 Country of ref document: EP |
|
| WWG | Wipo information: grant in national office |
Ref document number: 1019997005915 Country of ref document: KR |
|
| WWR | Wipo information: refused in national office |
Ref document number: PV1999-2347 Country of ref document: CZ |