EP4584318A1 - Silicone coating composition with mica - Google Patents

Silicone coating composition with mica

Info

Publication number
EP4584318A1
EP4584318A1 EP23805355.7A EP23805355A EP4584318A1 EP 4584318 A1 EP4584318 A1 EP 4584318A1 EP 23805355 A EP23805355 A EP 23805355A EP 4584318 A1 EP4584318 A1 EP 4584318A1
Authority
EP
European Patent Office
Prior art keywords
mica
composition
resin
dimethylsiloxane
terminated poly
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
EP23805355.7A
Other languages
German (de)
French (fr)
Inventor
Yanhu WEI
Peng-Fei Fu
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 Silicones Corp
Original Assignee
Dow Silicones Corp
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 Silicones Corp filed Critical Dow Silicones Corp
Publication of EP4584318A1 publication Critical patent/EP4584318A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
    • 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
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • the present invention relates to a composition
  • a composition comprising an MQ resin, a ZO-terminated poly(dimethylsiloxane), and mica, wherein the weight-to-weight ratio of the MQ resin to the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 10:90, and the weight-to-weight ratio of the mica to the sum of the MQ resin and the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 30:70, where each Z is independently H, Ci-C4-alkyl, or C(O)CH3.
  • the composition of the present invention is useful as a coating for a substrate, wherein the coating, when cured, exhibits adhesion and crack-resistance when subjected to high temperatures for hundreds of hours.
  • the present invention relates to a composition
  • a composition comprising an MQ resin, a ZO-terminated poly (dimethylsiloxane-), and mica, wherein the weight-to- weight ratio of the MQ resin to the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 10:90, and the weight-to- weight ratio of the mica to the sum of the MQ resin and the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 30:70, where each Z is independently H, Ci-C 4 -alkyl, or C(O)CH 3 .
  • MQ resiri refers to a kinetically stable three-dimensional polymer having repeat units of SiO 4 /2 (Q), and a plurality of tri-Ci-C 4 -alkylsilyl, preferably trimethylsilyl capping groups (M).
  • the resin may include additional capping groups such as CiC 4 -alkyl, dimethylhydroxysilyl, and dimethylvinylsilyl capping groups.
  • An example of commercially available MQ resins are DOWSILTM MQ-1600, MQ-1601, and MQ-1640 Resins (A Trademark of The Dow Chemical Company or its affiliates).
  • ZO-PDMS-OZ The ZO-terminated poly(dimethylsiloxane) (ZO-PDMS-OZ) can be illustrated by the following structure: where n is preferably from 20 or from 40 or from 70 or from 100, to 300 or to 250 or to 200.
  • the weight-to-weight ratio of the MQ resin to the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 or from 50:50 or from 40:60 to 10:90 or to 20:80 or to 25:75.
  • the composition of the present invention advantageously further comprises a crosslinking agent such as a Ci-C 4 -alkyl tri-Ci-C 4 -alkoxy silane, preferably methyltrimethoxysilane (MTMS), and a moisture cure catalyst to promote curing of the composition after it is applied as a coating onto a substrate.
  • a crosslinking agent such as a Ci-C 4 -alkyl tri-Ci-C 4 -alkoxy silane, preferably methyltrimethoxysilane (MTMS)
  • MTMS methyltrimethoxysilane
  • moisture cure catalysts include organotin and organotitanate catalysts such as tin octanoate, tin butanoate, tetraisopropyl titanate, tetra-/?-butyl titanate, and tetra-z-butoxy titanate.
  • This curable composition may be prepared by first blending the MQ resin, the ZO-PDMS-OZ, the crosslinking agent, and the moisture cure catalyst in the presence of a solvent to tune the viscosity to a desired level, preferably in the range of from 20 cP or from 50 cP or from 100 cP, to 20,000 cP or to 10,000 cP or to 5,000 cP, or to 1200 cP.
  • suitable solvents include aprotic solvents such as ethyl acetate, propyl acetate, butyl acetate, propyl propionate, and hexamethyldisiloxane (HMDS).
  • the blend is then advantageously contacted with the mica with additional blending, then applied to a substrate, such as a metal, metal oxide, ceramic, or glass substrate, at a desired coating thickness, typically in the range of from 10 pm or from 20 pm or from 50 pm to 200 pm or to 100 pm.
  • a substrate such as a metal, metal oxide, ceramic, or glass substrate
  • the coatings are then dried and subjected to thermal aging.
  • Aluminum panels (3” x 6”) were washed with toluene and acetone, then dried. A portion of the composition was applied at a thickness of 50 pm to 100 pm using a 4-mil drawdown bar.
  • the panels coated with the example formulations containing mica became tack free in 10 min at room temperature, while the panel coated with the mica-free formulation (Cl) became tack free in 1 h.
  • Each sample was then heated in an oven at 300 °C. Film cracking time was recorded (in days) as the first instance of visible cracks in the coatings.
  • Table 1 shows the thermal stability of coatings as measured by crack time.
  • the mica weight percent is based on the sum of the weights of the MQ resin, the HO-PDMS-OH, and the mica.
  • MQ resin and HO-PDMS-OH weight percentages are based on the sum of the MQ resin and HO-PDMS-OH.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention relates to a composition comprising an MQ resin, a ZO-terminated poly(dimethylsiloxane), and mica. The composition is useful as a coating on a substrate, wherein the coating exhibits adhesion, uniformity, and crack resistance when subjected to high temperatures for hundreds or even thousands of hours.

Description

Silicone Coating Composition with Mica
Background of the Invention
The present invention relates to a silicone coating composition, more particularly a composition that is resistant to cracking and dielectric degradation at high temperatures, and a method for preparing the composition. High temperature protective coatings and insulating materials to protect a variety of equipment and devices against extremely high temperatures. Heater elements for electric vehicles, exhaust systems for automotive engines, power plants, and top coatings for stoves, for example, all benefit from such protective coatings. In many applications, the coating layers must withstand temperatures exceeding 300 °C over several months without cracking or losing dielectric and insulating properties and must pass aggressive thermal shock tests over a broad temperature range.
High temperature resistance of silicones ostensibly makes them promising candidates as high temperature protective coatings and sealants; nevertheless, silicone rubbers are not resistant to cracking above 250 °C beyond 3 weeks. The combination of silicone and inorganic filler such as SiO2, TiO2, and AI2O3 provides a composition with long term high temperature resistance; however, coatings prepared from such compositions require aging at temperatures exceeding 500 °C to form ceramic-like coatings. At such extreme temperatures, the coatings are likely to crack and suffer thermal shock failure; moreover, electronic elements beneath the surface of the coating are vulnerable to damage. It would therefore be an advance in the field of high temperature protective coatings to develop a composition that provides a coating that is resistant to cracking, delamination, and thermal shock failure, while maintaining acceptable dielectric properties at temperatures exceeding 300 °C for an extended period.
Summary of the Invention
In one aspect, the present invention relates to a composition comprising an MQ resin, a ZO-terminated poly(dimethylsiloxane), and mica, wherein the weight-to-weight ratio of the MQ resin to the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 10:90, and the weight-to-weight ratio of the mica to the sum of the MQ resin and the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 30:70, where each Z is independently H, Ci-C4-alkyl, or C(O)CH3. The composition of the present invention is useful as a coating for a substrate, wherein the coating, when cured, exhibits adhesion and crack-resistance when subjected to high temperatures for hundreds of hours. Detailed Description of the Invention
The present invention relates to a composition comprising an MQ resin, a ZO-terminated poly (dimethylsiloxane-), and mica, wherein the weight-to- weight ratio of the MQ resin to the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 10:90, and the weight-to- weight ratio of the mica to the sum of the MQ resin and the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 30:70, where each Z is independently H, Ci-C4-alkyl, or C(O)CH3.
As used herein, the term “MQ resiri’ refers to a kinetically stable three-dimensional polymer having repeat units of SiO4/2 (Q), and a plurality of tri-Ci-C4-alkylsilyl, preferably trimethylsilyl capping groups (M). The resin may include additional capping groups such as CiC4-alkyl, dimethylhydroxysilyl, and dimethylvinylsilyl capping groups. An example of commercially available MQ resins are DOWSIL™ MQ-1600, MQ-1601, and MQ-1640 Resins (A Trademark of The Dow Chemical Company or its Affiliates).
The ZO-terminated poly(dimethylsiloxane) (ZO-PDMS-OZ) can be illustrated by the following structure: where n is preferably from 20 or from 40 or from 70 or from 100, to 300 or to 250 or to 200.
The weight-to-weight ratio of the MQ resin to the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 or from 50:50 or from 40:60 to 10:90 or to 20:80 or to 25:75.
Micas are hydrated aluminum silicate minerals including muscovite, biotite, fuchsite, phlogopite, margarite, glauconite, and lepidolite micas, of which muscovite mica and phlogopite mica are predominant. Muscovite mica has a typical composition of K2Al4(AhSi602o)(OH)4. The w/w ratio of the mica to the sum of the of the MQ resin and the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 or from 60:40, to 30:70 or 30:60.
The composition of the present invention advantageously further comprises a crosslinking agent such as a Ci-C4-alkyl tri-Ci-C4-alkoxy silane, preferably methyltrimethoxysilane (MTMS), and a moisture cure catalyst to promote curing of the composition after it is applied as a coating onto a substrate. Examples of moisture cure catalysts include organotin and organotitanate catalysts such as tin octanoate, tin butanoate, tetraisopropyl titanate, tetra-/?-butyl titanate, and tetra-z-butoxy titanate. This curable composition may be prepared by first blending the MQ resin, the ZO-PDMS-OZ, the crosslinking agent, and the moisture cure catalyst in the presence of a solvent to tune the viscosity to a desired level, preferably in the range of from 20 cP or from 50 cP or from 100 cP, to 20,000 cP or to 10,000 cP or to 5,000 cP, or to 1200 cP. Examples of suitable solvents include aprotic solvents such as ethyl acetate, propyl acetate, butyl acetate, propyl propionate, and hexamethyldisiloxane (HMDS). The blend is then advantageously contacted with the mica with additional blending, then applied to a substrate, such as a metal, metal oxide, ceramic, or glass substrate, at a desired coating thickness, typically in the range of from 10 pm or from 20 pm or from 50 pm to 200 pm or to 100 pm. The coatings are then dried and subjected to thermal aging.
During thermal aging, at least some portion of the MQ resin is observed to react with at least some portion of ZO-PDMS-OZ to form an MQ-PDMS copolymer. Thus, in another aspect, the present invention is a substrate coated with a composition comprising an MQ-PDMS copolymer and mica.
The composition of the present invention provides a tack-free coating in minutes that is thermally stable to cracking for hundreds or even thousands of hours.
Examples 1-5 - Preparation of Blend of MQ resin, Silanol-terminated PDMS, and Mica
DOWSIL™ MQ-1600 resin (Mo.45 Q0.55, 11.0 mole% SiOH), silanol-terminated PDMS (HO-PDMS-OH dp = 80), methyltrimethoxysilane (10 wt %, based on the total weight of the MQ-1600 resin, the silanol-terminated PDMS, and methyltrimethoxy silane), and a sufficient amount of hexamethyldisiloxane to adjust the viscosity of the mixture to 500 cp to 2000 cp were added to a dry flask under nitrogen. The mixture was stirred for 30 min, after which time mica, which had been dried in vacuo at 120 °C for 3 to 20 h then cooled to room temperature under nitrogen, was added to the mixture with stirring under nitrogen. MRX muscovite mica (MRX, median particle size 11.4 pm, obtained from Arctic Minerals) was used for Examples 1, 2, and 3, and C-4000 muscovite mica (C-4000, median particle size 10.8 pm, obtained from IMERYS) was used for examples 4 and 5. Tetraisopropyl titanate (1 wt% based on the weight of the formulation) was added to each sample with stirring. The comparative example formulation (Cl) did not include mica. Long Term High Temperature Resistance Testing
Aluminum panels (3” x 6”) were washed with toluene and acetone, then dried. A portion of the composition was applied at a thickness of 50 pm to 100 pm using a 4-mil drawdown bar. The panels coated with the example formulations containing mica became tack free in 10 min at room temperature, while the panel coated with the mica-free formulation (Cl) became tack free in 1 h. Each sample was then heated in an oven at 300 °C. Film cracking time was recorded (in days) as the first instance of visible cracks in the coatings.
Table 1 shows the thermal stability of coatings as measured by crack time. The mica weight percent is based on the sum of the weights of the MQ resin, the HO-PDMS-OH, and the mica. MQ resin and HO-PDMS-OH weight percentages are based on the sum of the MQ resin and HO-PDMS-OH.
Table 1 - Thermal Stability of Coatings
The data show that the cured coatings containing mica exhibit a dramatic resistance to cracking and delamination. Also, samples containing mica cured much faster than the sample without mica. The combination of the MQ resin and mica alone was found to fail the cracking test within 2 d, while the combination of the HO-PDMS-OH and mica alone delaminated readily from the substrate at 300 °C. Moreover, of the fillers tested - silica, calcium carbonate, aluminum silicate, calcium silicate, alumina, ferric oxide, and mica - mica was found to be the only class of fillers to exhibit crack times beyond 120 h.

Claims

Claims:
1. A composition comprising an MQ resin, a ZO-terminated poly (dimethylsiloxane), and mica, wherein the weight-to-weight ratio of the MQ resin to the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 10:90, and the weight-to-weight ratio of the mica to the sum of the MQ resin and the ZO-terminated poly(dimethylsiloxane) is in the range of from 70:30 to 30:70, where each Z is independently H, Ci-C4-alkyl, or C(O)CH3.
2. The composition of Claim 1 wherein Z is H, and the ZO-terminated poly(dimethylsiloxane) has a degree of polymerization in the range of from 20 to 300.
3. The composition of Claim 2 wherein the mica is a muscovite or phlogopite mica, and wherein the weight-to-weight ratio of the mica to the sum of the MQ resin and the HO-terminated poly(dimethylsiloxane) is in the range of from 60:40 to 30:60.
4. The composition of Claim 3 wherein the weight-to-weight ratio of the MQ resin to the HO-terminated poly(dimethylsiloxane) is in the range of from 50:50 to 20:80.
5. The composition of Claim 3 wherein the mica is muscovite mica and the weight-to-weight ratio of the MQ resin to the ZO-terminated poly (dimethylsiloxane) is in the range of from 40:60 to 25:75.
6. The composition of any of Claims 1 to 5 which further comprises a crosslinking agent, a moisture cure catalyst, and a solvent.
7. The composition of Claim 6 wherein the crosslinking agent is methyltrimethoxysilane, the moisture cure catalyst is an organotin or an organotitanate catalyst, and the solvent is ethyl acetate, propyl acetate, butyl acetate, propyl propionate, or hexamethyldisiloxane.
8. An article comprising a substrate coated with the composition of Claim 6.
9. The article of Claim 8 wherein the substrate is a metal, a metal oxide, a ceramic, or glass.
10. The article of Claim 9 wherein the crosslinking agent is methyltrimethoxysilane, the moisture cure catalyst is an organotin or an organotitanate catalyst, and the solvent is ethyl acetate, propyl acetate, butyl acetate, propyl propionate, or hexamethyldisiloxane.
11. The article of Claim 10 wherein the coating is cured.
EP23805355.7A 2022-10-27 2023-10-12 Silicone coating composition with mica Pending EP4584318A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202263419744P 2022-10-27 2022-10-27
PCT/US2023/076643 WO2024091798A1 (en) 2022-10-27 2023-10-12 Silicone coating composition with mica

Publications (1)

Publication Number Publication Date
EP4584318A1 true EP4584318A1 (en) 2025-07-16

Family

ID=88778266

Family Applications (1)

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EP23805355.7A Pending EP4584318A1 (en) 2022-10-27 2023-10-12 Silicone coating composition with mica

Country Status (6)

Country Link
EP (1) EP4584318A1 (en)
JP (1) JP2025535928A (en)
KR (1) KR20250093322A (en)
CN (1) CN120051507A (en)
TW (1) TW202417585A (en)
WO (1) WO2024091798A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119081542B (en) * 2024-09-27 2025-05-27 江苏元凝新材料有限公司 High-temperature-resistant waterproof coating and preparation method thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4800127A (en) * 1987-03-26 1989-01-24 General Electric Company Thermal shock resistant silicone coating composition
US4929703A (en) * 1989-03-30 1990-05-29 Dow Corning Corporation Solventless silicone coating composition
JP7353026B2 (en) * 2018-08-14 2023-09-29 モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 Room temperature curable polyorganosiloxane composition and cured product thereof

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JP2025535928A (en) 2025-10-30
WO2024091798A1 (en) 2024-05-02
KR20250093322A (en) 2025-06-24
TW202417585A (en) 2024-05-01
CN120051507A (en) 2025-05-27

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