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WO2025178762A1 - Générateur photo-acide fonctionnalisé par alkylsilyle - Google Patents

Générateur photo-acide fonctionnalisé par alkylsilyle

Info

Publication number
WO2025178762A1
WO2025178762A1 PCT/US2025/014741 US2025014741W WO2025178762A1 WO 2025178762 A1 WO2025178762 A1 WO 2025178762A1 US 2025014741 W US2025014741 W US 2025014741W WO 2025178762 A1 WO2025178762 A1 WO 2025178762A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
nmr
compound
mhz
mixture
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/US2025/014741
Other languages
English (en)
Inventor
Souvagya BISWAS
Debarshi CHAKRABORTY
Yanhu WEI
Peng-Fei Fu
Asim Maity
Sukrit MUKHOPADHYAY
David S. LAITAR
Tomas D. PAINE
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 WO2025178762A1 publication Critical patent/WO2025178762A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • C08K5/54—Silicon-containing compounds
    • C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
    • 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

Definitions

  • the present invention relates to a compound which is an alkylsilyl functionalized photo-acid generator.
  • Polyorganosiloxanes functionalized with epoxy groups can be cured by UV irradiation; such systems are attractive because, unlike free-radical polymerization, UV-induced polymerization of epoxides proceeds rapidly and with high oxygen tolerance; moreover, once UV curing has been initiated, it can be continued in the dark, long after initial UV irradiation has ceased.
  • UV curable epoxide systems proceed through a Cationic Ring Opening Epoxide Polymerization (CREOP) mechanism.
  • CREOP Cationic Ring Opening Epoxide Polymerization
  • R is either C1-C6-alkyl or -Y-CH2CH2-Si(R 3 )3;
  • R 1 and R 2 are each independently H, C1-C6-alkyl, or -X-Z-CH2CH2Si(R 3 )3; where each R 3 is independently C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, -OSi(C 1 -C 6 -alkyl), or phenyl;
  • X is Si(CH3)2 or CH2;
  • Y is a divalent C1-C12-hydrocarbyl group;
  • Z is a bond or a divalent C 1 -C 12 -hydrocarbyl group; and each M ⁇ is a borate, phosphate, arsenate, or antimonate anion; with the proviso that when R is -Y-CH 2 CH 2 -Si(R)3;
  • R 1 and R 2 are each independently H, C1
  • the compound of the present invention is useful as a photo-acid generator.
  • the present invention is a compound of Formula 1: OR where R is either C1-C6-alkyl or -Y-CH2CH2-Si(R 3 )3; R 1 and R 2 are each independently H, C 1 -C 6 -alkyl, or -X-Z-CH 2 CH 2 Si(R 3 ) 3 ; where each R 3 is independently C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, -OSi(C 1 -C 6 -alkyl), or phenyl; X is Si(CH3)2 or CH2; Y is a divalent C1-C12-hydrocarbyl group; Z is a bond or a divalent C 1 -C 12 -hydrocarbyl group; and each M ⁇ is a borate, phosphate, arsenate, or antimonate anion; with the proviso that when R is
  • R is -Y-CH2CH2-Si(R 3 )3, and R 1 and R 2 are H.
  • suitable R 3 groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, methoxy, ethoxy, n-butoxy, OSi(CH 3 ) 3 , and phenyl groups, as well as combinations thereof.
  • divalent hydrocarbyl group is used herein to describe an unsubstituted linear or branched divalent hydrocarbyl group or a linear or branched divalent hydrocarbyl group incorporated with an oxygen atom or a dimethylsilyl group.
  • suitable M ⁇ groups include SbF6 ⁇ , PF6 ⁇ , B[C6H3(CF3)2]4 ⁇ , and B(C6F5)4 ⁇ groups.
  • Table 1 illustrates compatibility and short time curability of example and comparative example PAGs.
  • “n” refers to the degree of polymerization (dp) of the epoxy-functionalized polymer.
  • Comp.1 and Comp.2 refer to the comparative PAGs, which have the following structures: Table 1 – Compatibility and Cure Data for PAGs and Epoxy-Functionalized Polyorganosiloxanes PAG Ex. M CEP D n M CEP dp M CEP D n M Vi dp Compatibility UV cure?

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)

Abstract

La présente invention concerne un composé de formule 1 : Formule (1), R, R1, R2 et M- étant tels que définis dans la description. Le composé de la présente invention est utile en tant que générateur photo-acide.
PCT/US2025/014741 2024-02-23 2025-02-06 Générateur photo-acide fonctionnalisé par alkylsilyle Pending WO2025178762A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202463557032P 2024-02-23 2024-02-23
US63/557,032 2024-02-23

Publications (1)

Publication Number Publication Date
WO2025178762A1 true WO2025178762A1 (fr) 2025-08-28

Family

ID=94924852

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2025/014741 Pending WO2025178762A1 (fr) 2024-02-23 2025-02-06 Générateur photo-acide fonctionnalisé par alkylsilyle

Country Status (2)

Country Link
TW (1) TW202534078A (fr)
WO (1) WO2025178762A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5468890A (en) * 1991-12-20 1995-11-21 Wacker-Chemie Gmbh Iodonium salts and process for the preparation thereof
US5703137A (en) 1996-03-14 1997-12-30 Rhone-Poulenc Chimie Initiators for the cationic crosslinking of polymers containing organofunctional groups
EP1136533A1 (fr) * 2000-01-28 2001-09-26 General Electric Company Compositions de silicones réticulables contenant des sels onium photoactifs
US20110070438A1 (en) * 2005-04-12 2011-03-24 Maneesh Bahadur Epoxy-Functional Polysiloxanes, Silicone Composition, and Coated Optical Fiber

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5468890A (en) * 1991-12-20 1995-11-21 Wacker-Chemie Gmbh Iodonium salts and process for the preparation thereof
US5703137A (en) 1996-03-14 1997-12-30 Rhone-Poulenc Chimie Initiators for the cationic crosslinking of polymers containing organofunctional groups
EP1136533A1 (fr) * 2000-01-28 2001-09-26 General Electric Company Compositions de silicones réticulables contenant des sels onium photoactifs
US20110070438A1 (en) * 2005-04-12 2011-03-24 Maneesh Bahadur Epoxy-Functional Polysiloxanes, Silicone Composition, and Coated Optical Fiber

Also Published As

Publication number Publication date
TW202534078A (zh) 2025-09-01

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