WO2026030700A1 - Acide dimère en tant qu'auxiliaire de traitement de polymère pour polyéthylène - Google Patents

Acide dimère en tant qu'auxiliaire de traitement de polymère pour polyéthylène

Info

Publication number
WO2026030700A1
WO2026030700A1 PCT/US2025/040329 US2025040329W WO2026030700A1 WO 2026030700 A1 WO2026030700 A1 WO 2026030700A1 US 2025040329 W US2025040329 W US 2025040329W WO 2026030700 A1 WO2026030700 A1 WO 2026030700A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkenyl
alkyl
carboxylic acid
terminal carboxylic
formula
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.)
Pending
Application number
PCT/US2025/040329
Other languages
English (en)
Inventor
Arkady L. Krasovskiy
Piyush Singh
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Publication of WO2026030700A1 publication Critical patent/WO2026030700A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/092—Polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/06—Properties of polyethylene
    • C08L2207/062—HDPE
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/06—Properties of polyethylene
    • C08L2207/066—LDPE (radical process)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2310/00—Masterbatches

Definitions

  • the present disclosure generally relates to formulations comprising ethylene-based polymer and dimer acids and are specifically related to the use of these formulations to reduce melt fracture during extrusion.
  • Plastics are used for a wide range of industrial applications, including packaging, construction, and wire and cable.
  • melt fracture is a phenomenon wherein the surface of the plastic becomes distorted with undulations or irregularities.
  • Embodiments of the present disclosure address these and other needs by providing formulations for polymer processing aids comprising at least 90 wt.% ethylene-based polymer and dimer acid.
  • Dimer acid is a compound that is primarily obtained from tall oil, a byproduct of the paper industry. The tall oil fatty acid undergoes a process known as dimerization, resulting in dimer acid. Dimerization is achieved through the reaction of unsaturations on the tall oil (ene reactions, Diels Alder reactions). The dimer acid with a small component of trimer acid, small component of remaining unreacted monomeric acid, and potentially small amount of polycyclic dimer acid can then optionally be hydrogenated to remove any remaining unsaturations.
  • the formulation may also comprise a trimer acid.
  • the ethylene-based polymer may comprise linear low-density polyethylene, high- density polyethylene, or combinations thereof.
  • polymer may refer to a polymeric compound prepared by polymerizing monomers, whether of the same or a different type.
  • the generic term polymer thus embraces the term “homopolymer,” usually employed to refer to polymers prepared from only one type of monomer as well as “copolymer,” which refers to polymers prepared from two or more different monomers.
  • the term “interpolymer,” as used herein, refers to a polymer prepared by the polymerization of at least two different types of monomers.
  • the generic term interpolymer thus includes copolymers, and polymers prepared from more than two different types of monomers, such as terpolymers.
  • Blends mean a composition of two or more polymers. Such a blend may or may not be miscible. Such a blend may or may not be phase separated. Such a blend may or may not contain one or more domain configurations, as determined from transmission electron spectroscopy, light scattering, x-ray scattering, and any other method known in the art. Blends are not laminates, but one or more layers of a laminate may contain a blend. Such blends can be prepared as dry blends, formed in situ (e.g., in a reactor), melt blends, or using other techniques known to those of skill in the art.
  • polyethylene or “ethylene -based polymer” may refer to polymers comprising greater than 50% by mole of units which have been derived from ethylene monomer. This includes polyethylene homopolymers or copolymers (meaning units derived from two or more comonomers).
  • ethylene-based polymer Common forms of ethylene-based polymer known in the art include Low Density Polyethylene (LDPE); Linear Low Density Polyethylene (LLDPE); Ultra Low Density Polyethylene (ULDPE); Very Low Density Polyethylene (VLDPE); single-site catalyzed Linear Low Density Polyethylene, including both linear and substantially linear low density resins (m-LLDPE); Medium Density Polyethylene (MDPE); and High Density Polyethylene (HDPE).
  • LDPE Low Density Polyethylene
  • LLDPE Linear Low Density Polyethylene
  • ULDPE Ultra Low Density Polyethylene
  • VLDPE Very Low Density Polyethylene
  • m-LLDPE linear low Density Polyethylene
  • MDPE Medium Density Polyethylene
  • HDPE High Density Polyethylene
  • LLDPE includes both resins made using the traditional Ziegler-Natta catalyst systems and chromium-based catalyst systems as well as single-site catalysts, including, but not limited to, bis -metallocene catalysts (sometimes referred to as “m- LLDPE”), constrained geometry catalysts (CGC), and molecular catalysts.
  • Resins include linear, substantially linear, or heterogeneous polyethylene copolymers or homopolymers.
  • LLDPEs contain less long chain branching than LDPEs and includes the substantially linear ethylene polymers which are further defined in U.S. Patent 5,272,236, U.S. Patent 5,278,272, U.S.
  • Patent 5,582,923 and US Patent 5,733,155 the homogeneously branched linear ethylene polymer compositions such as those in U.S. Patent No. 3,645,992; the heterogeneously branched ethylene polymers such as those prepared according to the process disclosed in U.S. Patent No. 4,076,698; and/or blends thereof (such as those disclosed in US 3,914,342 or US 5,854,045).
  • the LLDPEs can be made via gasphase, solution-phase or slurry polymerization or any combination thereof, using any type of reactor or reactor configuration known in the art.
  • HDPE high density polyethylene
  • high density polyethylene refers to ethylene-based polymers having densities greater than 0.935 g/cc, which are generally prepared with Ziegler-Natta catalysts, chrome catalysts or even metallocene catalysts.
  • fluoropolymer refers to polymeric compounds comprising fluorine, and is intended to be interpreted broadly so as to include what might be referred to as oligomeric species.
  • the fluoropolymer may comprise molecules containing at least three, at least four, at least five, or at least six fluorine containing units.
  • melt fracture refers to the formation of defects on a polymeric extrudate under various processing conditions.
  • the defects may be any deviation from a smooth, glossy, regular extrudate.
  • parts per million or “ppm” refers to parts per million by weight.
  • polymer melt refers to polymers or polymer blends that are at temperatures above their glass transition temperature, i.e. the temperature below which the physical properties of the polymers change to those of a glassy or crystalline state, and usually above their melting temperature.
  • the polymer melts may present as highly viscous liquids, and may possess non-Newtonian or viscoelastic natures.
  • dimer acid refers to dicarboxylic acids that are prepared by dimerizing unsaturated fatty acids.
  • trimer acid refers to tricarboxylic acids prepared from unsaturated fatty acids.
  • Embodiments of the formulation may include at least 90 wt.% ethylene-based polymer and dimer acid.
  • the formulations described herein comprise a dimer acid.
  • the dimer acid may be present in a mixture comprising dimer acids and trimer acids Dimer acids may be present in a greater amount than trimer acids.
  • the mixture comprising the dimer acids and trimer acids comprise from a minimum of 51 wt.%, 60 wt.%, 70 wt.%, 80 wt.%, 90 wt.%, or 95 wt.% dimer acids to a maximum of 55 wt.%, 60 wt.%, 70 wt.%, 80 wt.%, 90 wt.%, 95 wt.%, or 100 wt.% dimer acids.
  • the mixture may also comprise some amount of monomeric acid (e.g., non-dimerized or non- trimerized carboxylic acid) in addition to the dimer acid and trimer acid, for example, less than 5 wt.%, less than 2 wt.%, or less 1 wt.% monomeric acid.
  • monomeric acid e.g., non-dimerized or non- trimerized carboxylic acid
  • the dimer acid may comprise the structure of Formula (I), Formula
  • Formula (II) is the hydrogenated dimer acid of Formula (I).
  • Ri comprises a C4-C12 alkyl or a C4-C12 alkenyl when R4 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with terminal carboxylic acid;
  • R2 comprises a C4-C12 alkyl or a C4-C12 alkenyl when R3 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R3 comprises a C4-C12 alkyl or a C4-C12 alkenyl when R2 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R4 comprises a C4-C12 alkyl or a C4-C12 alkenyl
  • the dimer acid may be a dimer acid composition having a CAS number of 61788-89-4. In one or more embodiments, the dimer acid comprises a dimer of oleic acid.
  • a formulation comprises a dimer acid wherein the dimer acid comprises the structure of any one of Formula (I), Formula (II), or Formula (III).
  • Ri may comprise a C4-C12 alkyl or a C4-C12 alkenyl when R4 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R2 may comprise a C4-C12 alkyl or a C4-C12 alkenyl when R3 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R3 may comprise, independently or simultaneously, a C4-C12 alkyl or a C4-C12 alkenyl when R2 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R4 comprises a C4-C12 alkyl or a C4-C12 alkenyl when Ri
  • Ri may comprise a C4-C12 alkyl or a C4-C12 alkenyl when R4 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R2 may comprise a C4-C12 alkyl or a C4-C12 alkenyl when R3 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • the dimer acid is in a mixture having a majority of the structure of Formula (I) for non-hydrogenated dimer acid or Formula (II) for hydrogenated dimer acid.
  • the formulations described herein may further comprise a trimer acid.
  • the trimer acid may comprise the structure of Formula (IV), Formula (V), or mixtures thereof. As shown, Formula (V) is the hydrogenated trimer acid of Formula (IV).
  • Ri comprises a C4-C12 alkyl or a C4-C12 alkenyl when R4 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R2 comprises a C4-C12 alkyl or a C4-C12 alkenyl when R3 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R3 comprises a C4-C12 alkyl or a C4-C12 alkenyl when R2 comprises a C4-C12 alkyl with a terminal carboxylic acid or a C4-C12 alkenyl with a terminal carboxylic acid;
  • R4 comprises a C4-C12 alkyl or a C4-C12 alkenyl when Ri comprises a C4-C12 alkyl with a terminal carboxylic
  • the formulations described herein may further comprise a monomeric fatty acid.
  • the ethylene-based polymer may comprise LLDPE, HDPE, or combinations thereof.
  • the ethylene-based polymer may comprise a melt index (I2) of less than 4.0 dg/min as measured according to ASTM D-1238 (190° C, loading of 2.16 kg).
  • the ethylene-based polymer may comprise a melt index of from 0.05 to 4.0 dg/10 min, from 0.05 to 3 dg/10 min, or from 0.05 to 2.5 dg/10 min.
  • the ethylene-based polymer may comprise a density from 0.850 to 0.950 g/cc, from 0.875 to 0.925 g/cc, from 0.890 to 0.920 g/cc.
  • the formulations described herein may comprise greater than 90 wt.%, greater than 92 wt.%, greater than 95 wt.%, greater than 97 wt.%, greater than 98 wt.%, or even greater than 99 wt.% ethylene-based polymer, based on the total weight of the formulation. In other embodiments, the formulations described herein may comprise less than 100 wt.%, less than 98 wt.%, less than 97 wt.%, less than 95 wt.%, less than 92 wt.%, or even less than 91 wt.% ethylene-based polymer, based on the total weight of the formulation.
  • the dimer acid may comprise less than or equal to 10 wt.% based on the total weight of the formulation.
  • the dimer acid salts may be present in formulation from a minimum of 0.001 wt.%, 0.01 wt.%, 0.1 wt.%, 1 wt.%, 2 wt.%, or 5 wt.% to a maximum of 0.1 wt.%, 0.5 wt.%, 1 wt.%, 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, or 10 wt.% based on the total weight of the formulation.
  • the formulation is used to reduce or completely eliminate melt fracture during extrusion.
  • the polymer processing aid (PPA) i.e., the dimer acid may be delivered in many forms, for example, PPA masterbatch, or as liquid.
  • PPA polymer processing aid
  • Further optional additives are contemplated for the PPA and/or the formulation encompassing the PPA.
  • suitable other additives include antioxidants, antistatic agents, stabilizing agents, nucleating agents, colorants, pigments, ultraviolet (UV) absorbers or stabilizers, flame retardants, compatibilizers, plasticizers, fdlers, processing aids, antifog additive, crosslinking agents (e.g., peroxides), and combinations thereof.
  • the dimer acid may be directly added as a liquid into the ethylene-based polymer.
  • the dimer acid may be added to the ethylene -based polymer via a masterbatch.
  • generating a masterbatch may comprise compounding a polyethylene resin with the dimer acid.
  • the masterbatch may be combined with a base resin to reduce melt fracture in the base resin in an extruder to fabricate a finished article.
  • the base resin may include ethylene-based polymer, for example, FFDPE, FDPE, HDPE, or combinations thereof.
  • the LLDPE Resin used as the base resin and as the PPA masterbatch carrier for the inventive examples had a melt index (I2) of 2.3 dg/10 min and a density of 0.917 g/cc.
  • the dimer acid (also commercially available from Cargill) was obtained from Sigma Aldrich and is a hydrogenated dimer acid having a CAS Number of 68783-41-5.
  • the hydrogenated dimer acid comprises greater than 98.0 % Dimer and less than 2 % trimer with small amount of monomeric fatty acids (about 1 wt.% or less).
  • DynamarTM FX 5920 A is a fluoropolymer based PPA masterbatch available from 3MTM.
  • the base TTDPE resin was extruded via a single screw extruder into a 2 mm diameter capillary die.
  • the flow rate was 0.5 kg/hr, which at a melt temperature of 212 °C, translates approximately to a shear rate of about 269 s' 1 .
  • the resulting extrudate had melt fracture.
  • the PPA was introduced at loading levels listed in Table 3.
  • a timer was started when each formulation was introduced in the extruder after the process was stabilized. If melt fracture was not cleared after a maximum observable timeframe of 120 minutes, the timer was stopped. The time to clear melt fracture, concentration of the PPA added and peak temperature is shown in Table 3. After every formulation, the extruder was purged with the base resin until the melt fracture was fully re-established; confirmed visually as well by the stabilization of the processing conditions (extruder torque, pressure).
  • sample CE1 which contained fluoropolymer, cleared the melt fracture in 34 minutes.
  • samples IE1-IE5 which contain the dimer acid, exemplified better performance than CE1 for the time needed to clear melt fracture even at much lower loadings.
  • peak temperature and amperage decrease, which results in energy savings for customer and reduction of gels and cross-linking because of lower processing temperature. This is particularly notable, as samples IE1-IE5 contained notably lower amounts of PPA than CEE

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Des modes de réalisation d'une formulation comprennent au moins 90 % en poids de polymère à base d'éthylène et d'acide dimère, l'acide dimère étant un auxiliaire de traitement de polymère utilisé pour réduire la fracture de fusion pendant l'extrusion.
PCT/US2025/040329 2024-08-02 2025-08-01 Acide dimère en tant qu'auxiliaire de traitement de polymère pour polyéthylène Pending WO2026030700A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202463678804P 2024-08-02 2024-08-02
US63/678,804 2024-08-02

Publications (1)

Publication Number Publication Date
WO2026030700A1 true WO2026030700A1 (fr) 2026-02-05

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Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3645992A (en) 1967-03-02 1972-02-29 Du Pont Canada Process for preparation of homogenous random partly crystalline copolymers of ethylene with other alpha-olefins
US3914342A (en) 1971-07-13 1975-10-21 Dow Chemical Co Ethylene polymer blend and polymerization process for preparation thereof
US4076698A (en) 1956-03-01 1978-02-28 E. I. Du Pont De Nemours And Company Hydrocarbon interpolymer compositions
EP0055687A1 (fr) * 1980-12-29 1982-07-07 Allied Corporation Amorces de cristallisation pour des polymères cristallins
US5272236A (en) 1991-10-15 1993-12-21 The Dow Chemical Company Elastic substantially linear olefin polymers
US5278272A (en) 1991-10-15 1994-01-11 The Dow Chemical Company Elastic substantialy linear olefin polymers
US5582923A (en) 1991-10-15 1996-12-10 The Dow Chemical Company Extrusion compositions having high drawdown and substantially reduced neck-in
US5733155A (en) 1995-07-28 1998-03-31 The Whitaker Corporation Female contact
US5854045A (en) 1994-05-12 1998-12-29 The Rockefeller University Transmembrane tyrosine phosphatase and methods of use thereof
WO2005017022A1 (fr) * 2003-08-15 2005-02-24 E.I. Dupont De Nemours And Company Copolymeres ethylene/ester de vinyle a forte charge
WO2005056659A1 (fr) * 2003-11-12 2005-06-23 Cph Innovations Corp. Promoteur d'adhesion liquide pour du caoutchouc renforce par corde et composites substrat/caoutchouc metalliques ou polymeres associes
JP2012219402A (ja) * 2011-04-07 2012-11-12 Du Pont Mitsui Polychem Co Ltd 繊維材料の製造方法
CN106928453A (zh) * 2015-12-30 2017-07-07 江西省宜春远大化工有限公司 一种聚酰胺固化剂及其合成方法

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076698A (en) 1956-03-01 1978-02-28 E. I. Du Pont De Nemours And Company Hydrocarbon interpolymer compositions
US4076698B1 (fr) 1956-03-01 1993-04-27 Du Pont
US3645992A (en) 1967-03-02 1972-02-29 Du Pont Canada Process for preparation of homogenous random partly crystalline copolymers of ethylene with other alpha-olefins
US3914342A (en) 1971-07-13 1975-10-21 Dow Chemical Co Ethylene polymer blend and polymerization process for preparation thereof
EP0055687A1 (fr) * 1980-12-29 1982-07-07 Allied Corporation Amorces de cristallisation pour des polymères cristallins
US5278272A (en) 1991-10-15 1994-01-11 The Dow Chemical Company Elastic substantialy linear olefin polymers
US5272236A (en) 1991-10-15 1993-12-21 The Dow Chemical Company Elastic substantially linear olefin polymers
US5582923A (en) 1991-10-15 1996-12-10 The Dow Chemical Company Extrusion compositions having high drawdown and substantially reduced neck-in
US5854045A (en) 1994-05-12 1998-12-29 The Rockefeller University Transmembrane tyrosine phosphatase and methods of use thereof
US5733155A (en) 1995-07-28 1998-03-31 The Whitaker Corporation Female contact
WO2005017022A1 (fr) * 2003-08-15 2005-02-24 E.I. Dupont De Nemours And Company Copolymeres ethylene/ester de vinyle a forte charge
WO2005056659A1 (fr) * 2003-11-12 2005-06-23 Cph Innovations Corp. Promoteur d'adhesion liquide pour du caoutchouc renforce par corde et composites substrat/caoutchouc metalliques ou polymeres associes
JP2012219402A (ja) * 2011-04-07 2012-11-12 Du Pont Mitsui Polychem Co Ltd 繊維材料の製造方法
CN106928453A (zh) * 2015-12-30 2017-07-07 江西省宜春远大化工有限公司 一种聚酰胺固化剂及其合成方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
no. 68783-41-5

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