WO2023049485A1 - Thermoplastic polyolefin composition with reactive compatibilization - Google Patents

Thermoplastic polyolefin composition with reactive compatibilization Download PDF

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Publication number
WO2023049485A1
WO2023049485A1 PCT/US2022/044816 US2022044816W WO2023049485A1 WO 2023049485 A1 WO2023049485 A1 WO 2023049485A1 US 2022044816 W US2022044816 W US 2022044816W WO 2023049485 A1 WO2023049485 A1 WO 2023049485A1
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WO
WIPO (PCT)
Prior art keywords
based polymer
propylene
composition
ethylene
functionalized
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
Application number
PCT/US2022/044816
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English (en)
French (fr)
Inventor
Jeffrey C. Munro
Mark P. Allen
Santosh S. BAWISKAR
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
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Dow Global Technologies LLC
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Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to KR1020247013260A priority Critical patent/KR20240063989A/ko
Priority to CN202280061287.1A priority patent/CN117916307A/zh
Priority to EP22793304.1A priority patent/EP4408927B1/en
Priority to JP2024515634A priority patent/JP2024535225A/ja
Priority to US18/291,097 priority patent/US20240327632A1/en
Publication of WO2023049485A1 publication Critical patent/WO2023049485A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08L23/12—Polypropene
    • 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
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08L23/08—Copolymers of ethene
    • C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms
    • C08L23/0815—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms with aliphatic 1-olefins containing one carbon-to-carbon double bond
    • 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
    • C08L23/14—Copolymers of propene
    • 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—Ethylene-propylene or ethylene-propylene-diene copolymers
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • 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
    • C08L2207/02—Heterophasic composition

Definitions

  • DSC Differential Scanning Calorimetry
  • RCS refrigerated cooling system
  • autosampler was used to perform this analysis.
  • a nitrogen purge gas flow of 50 ml/min was used.
  • Each sample was melt pressed into a thin film at 190°C; the melted sample was then air-cooled to room temperature (25°C).
  • a 3-10 mg, 6 mm diameter specimen was extracted from the cooled polymer, weighed, placed in a light aluminum pan (ca 50 mg), and crimped shut. Analysis was then performed to determine its thermal properties.
  • Transmittance testing Total hemispherical luminous transmittance was measured according to ASTM D1003 using four-inch diameter, 0.125 inch thick injection molded discs. Transmittance is reported in percent, %.
  • the propylene-based polymer is a propylene impact copolymer.
  • the propylene impact copolymer is a heterophasic polymer wherein a rubber phase (or a discontinuous phase) of discrete domains of ethylene/propylene copolymer is dispersed throughout a matrix phase (or a continuous phase) of propylene homopolymer.
  • the propylene impact copolymer contains from 1 wt% to 40 wt%, or from 5 wt% to 25 wt%, or from 8 wt% to 15 wt% ethylene/propylene rubber phase, based on the total weight of the propylene impact copolymer.
  • the present functionalized propylene-based polymer may comprise two or more embodiments disclosed herein.
  • the functionalized ethylene-based polymer is made using an ethylene/Cs-Cs a-olefin copolymer ("base ethylene/Cs-Cs a-olefin copolymer”) having a density from 0.850 g/cc to 0.920 g/cc, or from 0.850 g/cc to 0.910 g/cc, or from 0.855 g/cc to 0.905 g/cc, or from 0.855 g/cc to 0.890 g/cc.
  • base ethylene/Cs-Cs a-olefin copolymer having a density from 0.850 g/cc to 0.920 g/cc, or from 0.850 g/cc to 0.910 g/cc, or from 0.855 g/cc to 0.905 g/cc, or from 0.855 g/cc to 0.890 g/cc.
  • the present composition may include one or more fillers.
  • suitable filler include talc, mica, calcium carbonate, nanoclay, carbon nanotube, carbon nanofiber, and combinations thereof.
  • the present composition further includes (D) the nonfunctionalized ethylene-based polymer.
  • the composition includes:
  • the composition includes
  • composition4 from 10 wt% to 25 wt%, or from 12 wt% to 25 wt% nonfunctionalized ethylenebased polymer (hereafter Composition ⁇ .
  • Composition4 has one, some, or all of the following properties:
  • (x) a transmittance from 35% to 70%, or from 50% to 60%.
  • compositions are void of, or is otherwise free of, thermoplastic polyurethane and/or a polymer containing isocyanate moiety.
  • Blends of the propylene-based polymers and ethylene-based polymers are immiscible.
  • the propylene-based polymers and the ethylene-based polymers form separate domains in the blend.
  • In-situ reaction between the functionalized propylene-based polymer and the functionalized ethylene-based polymer can improve the compatibility of the propylene-based polymer domains and the ethylenebased polymer domains and/or improve the interfacial strength between the propylene- based polymer domains and the ethylene-based polymer domains.
  • the functionalized ethylene-based polymer and/or the nonfunctionalized ethylene-based polymer can have higher density and a refractive index that more closely matches the refractive index of the nonfunctionalized propylene based polymer and functionalized propylene-based polymer, advantageously resulting in a light transmittance greater than 40% and suitable impact toughness for the present composition.
  • the present composition can be molded into an article.
  • Many types of molding operations can be used to form articles or parts from the present composition, including, but not limited to, injection molding, blow molding, compression molding, profile and sheet extrusion, and thermoforming.
  • the article is injection molded.
  • Nonlimiting examples of molded articles formed from the present composition include automotive interior and exterior components such as bumper fascia, airbag covers, door trim panels, instrument panels, seat backrests, exterior body panels (liftgate panels, door panels, fenders), rocker panels, cladding, wheel flares; household and personal articles such as freezer containers, storage containers, toys, electronics and computer parts, footwear components, and building materials.
  • the stream then entered a two stage separation and devolatilization system, where the polymer was removed from the solvent, hydrogen, and unreacted monomer and comonomer.
  • the solvent (plus dissolved components) was recycled.
  • the recycled stream was purified, before entering the reactor again.
  • the separated and devolatilized polymer melt was pumped through a die, and pelletized.
  • Table IB Molded article properties for molded articles made from the compositions of Table 1A
  • the inventive compositions have higher notched Izod impact strength and/or higher dart impact ductility, with higher or comparable modulus, and similar light transmittance as the comparative examples, demonstrating that the functionality can be present on ethylene-based polymers of a range of different density, melt index, and polymer type (i.e.
  • Table 5B Molded article properties for molded articles made from the compositions of Table 5A
  • Table 6A and Table 6B provide formulations based on nonfunctionalized propylene homopolymer (A) and also contain filler (E), namely, talc.
  • Table 6A includes the formulations and properties of the blends as prepared by Haake blending.
  • Table 6B includes properties of compression molded parts made from the compositions.
  • CS I is a formulation without either functionalized component.
  • CS J and CS K each contain only one of the functionalized components.
  • IE 8 with both functionalized components, has higher notched Izod impact strength, similar high shear rate viscosity, and lower tan 6 compared to CS I, J, and K.

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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)
PCT/US2022/044816 2021-09-27 2022-09-27 Thermoplastic polyolefin composition with reactive compatibilization Ceased WO2023049485A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1020247013260A KR20240063989A (ko) 2021-09-27 2022-09-27 반응성 상용성을 갖는 열가소성 폴리올레핀 조성물
CN202280061287.1A CN117916307A (zh) 2021-09-27 2022-09-27 具有反应性增容的热塑性聚烯烃组合物
EP22793304.1A EP4408927B1 (en) 2021-09-27 2022-09-27 Thermoplastic polyolefin composition with reactive compatibilization
JP2024515634A JP2024535225A (ja) 2021-09-27 2022-09-27 反応性相溶化を有する熱可塑性ポリオレフィン組成物
US18/291,097 US20240327632A1 (en) 2021-09-27 2022-09-27 Thermoplastic Polyolefin Composition with Reactive Compatibilization

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163248744P 2021-09-27 2021-09-27
US63/248,744 2021-09-27

Publications (1)

Publication Number Publication Date
WO2023049485A1 true WO2023049485A1 (en) 2023-03-30

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PCT/US2022/044816 Ceased WO2023049485A1 (en) 2021-09-27 2022-09-27 Thermoplastic polyolefin composition with reactive compatibilization

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Country Link
US (1) US20240327632A1 (https=)
EP (1) EP4408927B1 (https=)
JP (1) JP2024535225A (https=)
KR (1) KR20240063989A (https=)
CN (1) CN117916307A (https=)
WO (1) WO2023049485A1 (https=)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022115378A1 (en) * 2020-11-25 2022-06-02 Dow Global Technologies Llc. Polymer blends having increased temperature resistance
KR20260005692A (ko) * 2024-07-03 2026-01-12 롯데케미칼 주식회사 폴리올레핀 수지 조성물 및 이로부터 제조된 성형품

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5919983A (en) 1996-03-27 1999-07-06 The Dow Chemical Company Highly soluble olefin polymerization catalyst activator
US7608668B2 (en) 2004-03-17 2009-10-27 Dow Global Technologies Inc. Ethylene/α-olefins block interpolymers
WO2013048754A1 (en) * 2011-09-30 2013-04-04 Dow Global Technologies Llc Flame retardant thermoplastic composition of polycarbonate and polypropylene
WO2013090393A1 (en) * 2011-12-14 2013-06-20 Dow Global Technologies Llc Functionalized block composite and crystalline block composite compositions as compatibilizers
WO2018022975A1 (en) 2016-07-29 2018-02-01 Dow Global Technologies Llc Silyl-bridged bis-biphenyl-phenoxy catalysts for olefin polymerization

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5919983A (en) 1996-03-27 1999-07-06 The Dow Chemical Company Highly soluble olefin polymerization catalyst activator
US7608668B2 (en) 2004-03-17 2009-10-27 Dow Global Technologies Inc. Ethylene/α-olefins block interpolymers
WO2013048754A1 (en) * 2011-09-30 2013-04-04 Dow Global Technologies Llc Flame retardant thermoplastic composition of polycarbonate and polypropylene
WO2013090393A1 (en) * 2011-12-14 2013-06-20 Dow Global Technologies Llc Functionalized block composite and crystalline block composite compositions as compatibilizers
WO2018022975A1 (en) 2016-07-29 2018-02-01 Dow Global Technologies Llc Silyl-bridged bis-biphenyl-phenoxy catalysts for olefin polymerization

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BERNHARD WUNDERLICH: "The Basis of Thermal Analysis, in Thermal Characterization of Polymeric Materials", vol. 92, 1997, pages: 278 - 279

Also Published As

Publication number Publication date
EP4408927A1 (en) 2024-08-07
JP2024535225A (ja) 2024-09-30
EP4408927B1 (en) 2026-01-14
US20240327632A1 (en) 2024-10-03
KR20240063989A (ko) 2024-05-13
CN117916307A (zh) 2024-04-19

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