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WO2025165568A1 - Pré-catalyseur de platine(iv) à fonction siloxane - Google Patents

Pré-catalyseur de platine(iv) à fonction siloxane

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Publication number
WO2025165568A1
WO2025165568A1 PCT/US2025/011559 US2025011559W WO2025165568A1 WO 2025165568 A1 WO2025165568 A1 WO 2025165568A1 US 2025011559 W US2025011559 W US 2025011559W WO 2025165568 A1 WO2025165568 A1 WO 2025165568A1
Authority
WO
WIPO (PCT)
Prior art keywords
phenyl
independently
alkyl
osi
methyl
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/US2025/011559
Other languages
English (en)
Inventor
Mary E. Garner
Jonathan AXTELL
Souvagya BISWAS
Bizhong Zhu
Myoungbae LEE
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
Dow Silicones Corp
Original Assignee
Dow Global Technologies LLC
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 Global Technologies LLC, Dow Silicones Corp filed Critical Dow Global Technologies LLC
Publication of WO2025165568A1 publication Critical patent/WO2025165568A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2291—Olefins
    • 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
    • C08F4/72—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44
    • C08F4/80—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from iron group metals or platinum group metals
    • 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
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/398—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing boron or metal atoms
    • 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
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H19/32—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
    • 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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups

Definitions

  • the present invention relates to a photoactivated siloxane-functionalized platinum (IV) (Pt(IV)) pre-catalyst, particularly for hydrosilylation reactions.
  • Hydrosilylation is commonly used in the silicones industry for the synthesis of silicone polymers and cross-linked materials.
  • UV-initiated hydrosilylation using a photoactive pre-catalyst is becoming more popular as the energy input needed to trigger the reaction is low relative to thermally activated approaches.
  • Pt(IV) species such as cyclopentadienyltrimethylplatinum and its analogs are known as photoactive pre- catalysts (see US 4,510,094; US 8,088,878; and US 10,392,479) for hydrosilylation; Pt(IV) decompose under UV irradiation to form the catalytically active Pt(0) species. Nevertheless, these known pre-catalysts are often undesirably volatile and reactions using these pre-catalysts tend to be sluggish.
  • Pt(IV) species such as cyclopentadienyltrimethylplatinum and its analogs are known as photoactive pre-catalysts (see US 4,510,094; US 8,088,878; and US 10,392,479) for hydrosilylation; Pt(IV) decompose under UV irradiation to form the catalytically active Pt(0) species. Nevertheless, these known pre-catalysts are often undesirably volatile and reactions using these pre-catalysts tend to be sluggish.
  • the present invention is a compound of Formula 1: where Ar is phenyl, naphthyl, or anthracenyl; X is a C2-C12 hydrocarbyl diradical; each R 1 is independently C 1 -C 6 -alkyl or phenyl; each R 2 is independently C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, Ar, NO2, acetyl, trifluoromethyl, or halo; each R 3 is independently C1-C6-alkyl, C1-C6-alkoxy, phenyl, or -(OSi(R 5 ) 2 ) w OSi(R 6 ) 3 ; each R 4 is independently C 1 -C 6 -alkyl, phenyl, or C 1 -C 6 -alkoxy; each R 5 is independently C1-C6-alkyl, phenyl, or OSi(R 4 )3; each R 6 is independently C1
  • the present invention addresses a need in the art by providing a Pt(IV) pre-catalyst that decomposes rapidly to the catalytically active Pt(0) state under light irradiation.
  • the present invention is a compound of Formula 1: where Ar is phenyl, naphthyl, or anthracenyl; X is a C2-C12 hydrocarbyl diradical; each R 1 is independently C1-C6-alkyl or phenyl; each R 2 is independently C1-C6-alkyl, C1-C6-alkoxy, Ar, NO2, acetyl, trifluoromethyl, or halo; each R 3 is independently C1-C6-alkyl, C1-C6-alkoxy, phenyl, or -(OSi(R 5 )2)wOSi(R 6 )3; each R 4 is independently C1-C6-alkyl, phenyl, or C1-C6-al
  • each R 4 is methyl when z is from 1 to 20, and each R 4 is phenyl when z is 0; each R 5 is independently methyl, phenyl, or -OSi(OCH3)3; and each R 7 is H.
  • the compound of the present invention is advantageously prepared using the following steps.
  • an alkali metal cyclopentadiene such as sodium cyclopentadiene (Na-Cp) is contacted with R 1 -Br to form an alkyl or phenyl substituted cyclopentadiene (R 1 )x-Cp.
  • R 1 groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.
  • (R 1 )x-Cp is then contacted with an alkali metal bis(trimethylsilyl)amide such as potassium or sodium bis(trimethylsilyl)amide or with an alkyl lithium such as n-butyl lithium to form the alkali metal salt of (R 1 )x-Cp
  • an alkali metal bis(trimethylsilyl)amide such as potassium or sodium bis(trimethylsilyl)amide
  • an alkyl lithium such as n-butyl lithium
  • a dibromomethylaryl compound such as dibromomethylbenzene is contacted with an alkenyl-functionalized Grignard reagent to form an alkenyl-functionalized bromomethylaryl compound, preferably an alkenyl-functionalized bromomethylbenzene (Intermediate B): for the compound of Formula 1 where X is a C3-C12 hydrocarbyl diradical.
  • An analogous intermediate can be prepared where X is a C2 hydrocarbyl diradical by using the commercially available bromomethylstyrene as Intermediate B.
  • a tolyl-functionalized Grignard reagent such as (p-tolyl)magnesium bromide is contacted with a halide-functionalized dimethyl(vinyl)silyl compound such as chlorodimethyl(vinyl)silane to form a tolyl-functionalized dimethyl(vinyl)silyl compound:
  • the tolyl-functionalized dimethyl(vinyl)silyl compound can then be treated with a brominating agent such as N-bromosuccinimide (NBS) in the presence of a radical initiator such as azobisisobutyronitrile (AIBN) to generate a dimethyl(vinyl)silyl-functionalized bromomethylbenzene (Intermediate B′), where each R 7 is H and m is 1:
  • Intermediate B or B′ is advantageously contacted with a siloxane containing Si-H functionality, in the presence of a platinum catalyst to form Intermediate C:
  • a platinum catalyst to form Intermediate C:
  • Norbornadiene dimethyl platinum (II) ((NBD)PtMe 2 ) is dissolved in suitable donor solvent such as pyridine, then contacted with Intermediate C under conditions sufficient to form an oxidative addition product, which is then contacted in the same reaction vessel with Intermediate A to form the compound of Formula 1:
  • Ar is preferably or -(OSi(R 5 )2)wOSi(R 6 )3.
  • R 5 is preferably methyl, phenyl, or -OSi(OCH3)3; each R 6 is preferably methyl; each R 7 is preferably H; and the sum of z + w is preferably from 1 to 15. In another aspect, w is 0; in another aspect, z is from 1 to 15.
  • Specific examples of compounds of the present invention include the following:
  • Suitable pyridines include pyridine, 4-methylpyridine, 4-t-butylpyridine, 4-methoxypyridine, and 4-dimethylaminopyridine.
  • Suitable quinolines include quinoline, 8-methylquinoline, and 8-methoxyquinoline.
  • the compound of the present invention is a Pt(IV) pre-catalyst that exhibits excellent efficiency for promoting UV-triggered hydrosilylation chemistry.
  • the resulting colorless suspension was stored at -25 °C for 1 h prior to the dropwise addition of a 1.0 M solution of allylmagnesium bromide in diethyl ether (28.8 mL, 28.8 mmol, 0.95 equiv) to the suspension.
  • the resulting gray suspension was allowed to warm to ambient temperature and stirred vigorously for 72 h.
  • the reaction mixture was then removed from the glovebox and diluted with deionized water (25 mL) causing the heterogenous mixture to become homogeneous.
  • the resulting biphasic mixture was transferred to a separatory funnel and the organic layer was washed with water (2 x 10 mL) and brine (2 x 10 mL).
  • Karstedt's catalyst was added (3 drops of a 2 wt% Pt in xylenes solution) and the mixture was heated to 50 °C, followed by the dropwise addition of 1,1,1,3,3-pentamethyldisiloxane (MM') (0.87 mL, 4.44 mmol, 1 equiv). Stirring was continued at 50 °C for 24 h. The mixture was cooled to room temperature then diluted with hexanes (4 mL) and stirred with activated carbon for 5 – 10 min. The mixture was then passed through a 0.45- ⁇ m PTFE syringe filter and the volatiles were removed by rotary evaporation to afford a nearly colorless liquid.
  • MM' 1,1,1,3,3-pentamethyldisiloxane
  • Karstedt's catalyst was added (2 drops of a 2wt% Pt in xylenes) and the mixture was heated to 50 °C followed by the dropwise addition of 1,1,1,3,5,5,5-heptamethyltrisiloxane (MD′M) (0.217 mL, 0.80 mmol, 1 equiv). After 2 h, the mixture was cooled to ambient temperature, and the reaction mixture was diluted with hexanes (4 mL) and stirred with activated carbon for 5 – 10 min. The mixture was then passed through a 0.45- ⁇ m PTFE syringe filter and the volatiles were removed by rotary evaporation to afford a nearly colorless liquid. Yield: 0.338 g, 94.4 %.
  • MD′M 1,1,1,3,5,5,5-heptamethyltrisiloxane
  • reaction mixture was then heated a total of 18 h at 70 °C, after which time the reaction mixture was cooled to ambient temperature and then concentrated in vacuo onto silica gel and purified by ISCO chromatography using 100 % hexanes at the solvent system.
  • the desired product was isolated from fractions 5 - 11. Yield: 0.360 g, 22.6 %.
  • Karstedt's catalyst was added (1 drop of a 2 wt% Pt in xylenes) and the mixture was heated to 50 °C followed by the dropwise addition of 1,1,1,3,5,5,5-heptamethyltrisiloxane (MD′M) (0.112 mL, 0.41 mmol, 1 equiv). After 2 h, the mixture was cooled to ambient temperature, and the reaction mixture was diluted with hexanes (4 mL) and stirred with activated carbon for 5 min. The mixture was then passed through a 0.45- ⁇ m PTFE syringe filter and the volatiles were removed by rotary evaporation to afford a nearly colorless liquid. Yield: 0.183 g, 93.1 %.
  • MD′M 1,1,1,3,5,5,5-heptamethyltrisiloxane
  • Example 1 Preparation of CpPtMe2-benzyl-MM (NBD)PtMe2 (0.20 g, 0.63 mmol, 1 equiv) was combined with pyridine (5 mL) and a magnetic stir bar in a 20-mL glass vial in a nitrogen filled glovebox. The resulting golden yellow solution was allowed to stir at ambient temperature for 5 min, after which time Br-benzyl-MM (Intermediate 3, 0.235 g, 0.63 mmol, 1 equiv) was added dropwise. After stirring for another 4 h, NaCp (0.067 g, 0.76, 1.2 equiv) was added to the reaction mixture directly as a solid at ambient temperature. The reaction mixture was stirred at ambient temperature for 18 h.
  • Example 2 Preparation of (CH 3 ) 5 -CpPtMe 2 -(benzyl-MM) (NBD)PtMe 2 (0.130 g, 0.41 mmol, 1 equiv) was combined with pyridine (3 mL) and a magnetic stir bar in a 20-mL glass vial in a nitrogen filled glovebox. The resulting golden yellow solution was allowed to stir at ambient for 10 min, after which time Br-benzyl-MM (0.153 g, 0.41 mmol, 1 equiv) was added dropwise to the solution.
  • Li(CH3)5Cp (0.070 g, 0.49, 1.2 equiv) was added to the reaction mixture directly as a solid at ambient temperature. Additional pyridine (2 mL) was added to facilitate quantitative transfer of all the Cp salt into the reaction vial. The reaction mixture was stirred at ambient temperature for another 2 h, after which time the reaction mixture was passed through a Celite pad atop a Florisil pad contained within a 0.45- ⁇ m PTFE syringe filter. The pads and filter were rinsed with hexanes (4 x 3 mL) and combined with the filtrate.
  • Li Me Cp (0.048 g, 0.56, 1.2 equiv) was added to the reaction mixture directly as a solid at ambient temperature.
  • the reaction mixture was stirred at ambient temperature for another 2 h, after which time the reaction mixture was then passed through a celite pad atop a Fluorisil pad and filtered through a 0.45- ⁇ m PTFE syringe filter. The pads and filter were rinsed with hexanes (4 x 3 mL) and combined with the filtrate.
  • Example 4 Preparation of CH 3 -CpPtMe 2 -(benzyl-MDM) (NBD)PtMe 2 (0.85 g, 0.27 mmol, 1 equiv) was combined with pyridine (2 mL) and a magnetic stir bar in a 20-mL glass vial in a nitrogen filled glovebox. The resulting golden yellow solution was allowed to stir at ambient for 20 min after which time Br-benzyl-MDM (0.120 g, 0.27 mmol, 1 equiv) in pyridine (0.5 mL) was added dropwise to the solution.
  • NBD benzyl-MDM
  • Example 5 Preparation of CH3-CpPtMe2-(benzyl-SiMe2-MDM) (NBD)PtMe2 (0.082 g, 0.26 mmol, 1 equiv) was combined with pyridine (2 mL) and a magnetic stir bar in a 30-mL glass vial. The resulting pale-yellow solution was allowed to stir at ambient for 20 min, whereupon Br-benzyl-SiMe2-MDM (0.123 g, 0.26 mmol, 1 equiv) was added dropwise. Additional pyridine (1 mL) was added to ensure quantitative transfer of the bromomethyl reagent to the reaction vial.
  • Li Me Cp (0.027 g, 0.31 mmol, 1.2 equiv) was added to the reaction mixture directly as a solid at ambient temperature.
  • the reaction mixture was allowed to continue stirring at ambient temperature for 1 h, whereupon the volatiles were removed in vacuo. Hexanes was added to the residue, affording a suspension that was then stirred for 1h at ambient temperature.
  • the suspension was then passed through a Florisil pad and a 0.45- ⁇ m PTFE syringe filter. The filtration pad was rinsed with hexanes (2 x 5 mL) and combined with the filtrate.
  • Examples 1-5 Pre-catalysts were combined separately with methyl trimethoxy silane (XIAMETERTM OFS-6070 Silane (MTM)). Each pre-catalyst + MTM mixture was added to a pre-mixed blend of a vinyl-terminated polydimethylsiloxane (XIAMETERTM RBL-9119 Polymer (Polymer 1)) and a trimethylsilyl-terminated methylhydrosiloxane-dimethylsiloxane copolymer (DOWSILTM 6-3570 Polymer (Polymer 2). Each composition was mixed at 2000 rpm for 30 s.
  • Table 1 illustrates the formulations.
  • Formulation 1 used the compound of Example 1;
  • Formulation 2 used the compound of Example 2, etc.
  • Pre-catalyst + Solvent amounts were tuned to achieve a concentration of elemental Pt of 18 ppm for each formulation.
  • the pre-catalyst concentration in MTM refers to the weight % concentration of the pre-catalyst.
  • Table 1 Polyorganosiloxane Formulations Formulation Example No.
  • UV-rheology test UV-activated hydrosilylation cure tests were carried out using an MCR-302 Rheometer equipped with a UV irradiation accessory. Broadband UV of a wavelength between 250 and 450 nm was irradiated, and 4 J/cm 2 of UV dose was applied (100 mW/cm 2 x 40 sec). Sample thickness was initially set at 0.3 mm. To generate cure profiles, viscoelastic properties were monitored applying oscillatory shearing within linear viscoelastic regions at 10 rad/sec. Then, the gel times were determined from the G’-G” crossover points. Table 2 illustrates the gel point times for each formulation.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)

Abstract

La présente invention concerne un composé de formule 1 dans laquelle Ar, X, R1, R2, R3, R4, R7, x, y, et z sont tels que définis dans la description. La présente invention concerne un pré-catalyseur qui se décompose rapidement à un état de platine qui favorise l'hydrosilylation lors de l'exposition à une lumière de longueur d'onde appropriée.
PCT/US2025/011559 2024-01-31 2025-01-14 Pré-catalyseur de platine(iv) à fonction siloxane Pending WO2025165568A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202463627487P 2024-01-31 2024-01-31
US63/627,487 2024-01-31

Publications (1)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4510094A (en) 1983-12-06 1985-04-09 Minnesota Mining And Manufacturing Company Platinum complex
US8088878B2 (en) 2008-01-25 2012-01-03 Wacker Chemie Ag Hydrosilylation reactions activated through radiation
US10392479B2 (en) 2014-08-26 2019-08-27 Wacker Chemie Ag Platinum complexes and their use in compounds that can be cross-linked by a hydrosilylation reaction
WO2021168056A1 (fr) * 2020-02-19 2021-08-26 Momentive Performance Materials Inc. Compositions de silicone photodurcissables et procédé de fabrication de revêtements anti-adhésifs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4510094A (en) 1983-12-06 1985-04-09 Minnesota Mining And Manufacturing Company Platinum complex
US8088878B2 (en) 2008-01-25 2012-01-03 Wacker Chemie Ag Hydrosilylation reactions activated through radiation
US10392479B2 (en) 2014-08-26 2019-08-27 Wacker Chemie Ag Platinum complexes and their use in compounds that can be cross-linked by a hydrosilylation reaction
WO2021168056A1 (fr) * 2020-02-19 2021-08-26 Momentive Performance Materials Inc. Compositions de silicone photodurcissables et procédé de fabrication de revêtements anti-adhésifs

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE REAXYS [online] 1 January 2021 (2021-01-01), MOMENTIVE PERFORMANCE MATERIALS: "PHOTOCURABLE SILICONE COMPOSITIONS AND PROCESS FOR MANUFACTURE OF RELEASE LINERS - WO2021/168056", XP093254868, Database accession no. XRN = 52075105, 52075113 *
EUR. J. INORG. CHEM., vol. 2015, 2015, pages 226 - 239

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