Title:
β-DIKETONE CERIUM (IV) COMPOUND, AND PREPARATION AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/208951
Kind Code:
A1
Abstract:
Disclosed is a β-diketone cerium (IV) compound of formula (I). The compound has a wide absorption band, is suitable for near ultraviolet-visible region curing as a photoinitiator, and has a high sensitiveness, while also having the advantages of being low in toxicity, low in price, easily available, etc. Also disclosed are the preparation and the use of a compound of formula (I). The compound of formula (I) is particularly suitable for use as a photoinitiator in a UV-LED photocuring system, in particular for use as a photoinitiator in a photocuring system with a radiation wavelength of 300-600 nm.
Inventors:
ZOU YINGQUAN (CN)
GAO MING (CN)
PANG YULIAN (CN)
GAO MING (CN)
PANG YULIAN (CN)
Application Number:
PCT/CN2021/087181
Publication Date:
October 21, 2021
Filing Date:
April 14, 2021
Export Citation:
Assignee:
HUBEI GURUN TECH CO LTD (CN)
International Classes:
C07C49/92; C07C45/77; C07C51/347; C07C59/185; C07C67/00; C07C69/716; C07C201/12; C07C205/45; C07C221/00; C07C225/06; C07C253/30; C07C255/17; C07C303/22; C07C309/07; C07C309/44; C07D213/50; C07D303/32; C07D307/46; C07D333/22; C08F2/48; C08F2/50; C08F122/20
Domestic Patent References:
| WO2021048044A1 | 2021-03-18 |
Foreign References:
| CN111302926A | 2020-06-19 | |||
| JPS5232984A | 1977-03-12 | |||
| US4036605A | 1977-07-19 |
Other References:
STILINOVIĆ VLADIMIR, KAITNER BRANKO: "Two tetrakis(benzoylacetonato)lanthanide species: synthesis, characterization and structures of tetrakis(benzoylacetonato)cerium(IV) and triethylammonium tetrakis(benzoylacetonato)lanthanate(III) tetrahydrate", JOURNAL OF COORDINATION CHEMISTRY, TAYLOR & FRANCIS, LONDON, vol. 62, no. 16, 20 August 2009 (2009-08-20), London , pages 2698 - 2708, XP055858811, ISSN: 0095-8972, DOI: 10.1080/00958970902912365
DELAROSA MARK, BOUSMAN KENNETH, WELCH JOHN, TOSCANO PAUL: "Physical and Structural Characterization of Ce(IV) β -Diketonate Complexes: Evidence for Geometrical Isomers in the Solid-State", JOURNAL OF COORDINATION CHEMISTRY, TAYLOR & FRANCIS, LONDON, vol. 55, no. 7, 1 January 2002 (2002-01-01), London , pages 781 - 793, XP055834856, ISSN: 0095-8972, DOI: 10.1080/0095897022000001539
BRILL GISELA, MUSSO HANS: "Anisotropieeffekte in den 1H-NMR-Spektren 3-mesitylsubstituierter Acetylaceton-Metallchelate, II", LIEBIGS ANNALEN DER CHEMIE, vol. 1979, 29 June 1979 (1979-06-29), pages 803 - 810, XP055834980, DOI: 10.1002/jlac.197919790610
KASTNING E G, NAARMANN H, REIS H, BERDING C: "Metal Chelates as Polymerization Initiators", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 4, no. 4, 1 April 1965 (1965-04-01), pages 322 - 327, XP055858823, ISSN: 1521-3773, DOI: 10.1002/anie.196503221
BAXTER IAN ET AL.: "Preparation and Crystal Structures of the Ce(IV) β-Diketonates, [Ce(tmhd)4] and [Ce(pmhd)4] (Tmhd = 2, 2, 6, 6-Tetramethylheptane-3, 5-Dionate and Pmhd = 1-Phenyl-5-Methylhexane-1, 3-Dionate)", JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol. 28, no. 4, 1 April 1998 (1998-04-01), XP055834855, ISSN: 1572-8854
MCCARLEY R E, TEMPLETON J L, COLBURN T J, KATOVIC V, HOXMEIER R J, SHANKAR GOPALAN, RAMALINGAM SUTHAMALLI K: "Phenylisocyanation and Bromination Studies on Lanthanide Beta-Diketonates", TRANSITION METAL CHEMISTRY, vol. 9, no. 10, 1 December 1984 (1984-12-01), pages 449 - 453, XP055858268
TISCHER, ROBERT L, KENT J. EISENTRAUT KARL SCHELLER, ROBERT E. SIEVERS ROBERT C. BAUSMAN, PATRICIA R. BLUM: "New Rare Earth Antiknock Additives That are Potential Substitutes for Tetraethyl Lead (AD/A-O06 151)", AEROSPACE RESEARCH LABORATORIES - TECHNICAL REPORT, 1 December 1974 (1974-12-01), XP055858270
SCHILDCROUT STEVEN M: "Contribution from the Electron-Ionization Mass Spectra of Fluorinated Beta-Diketonate Complexes of Cerium(IV)+", INORGANIC CHEMISTRY, vol. 24, no. 5, 1 February 1985 (1985-02-01), pages 760 - 762, XP055858267
MUTHUKUMAR M, BALASUBRAMANIAN V: "Iodination, Bromination and Isocyanation Reactions of Beta-Diketonates of Lanthanum(III), Cerium(IV), Thorium(IV) and Uranyl(VI)", ASIAN JOURNAL OF CHEMISTRY, vol. 21, no. 1, 1 January 2009 (2009-01-01), pages 737 - 744, XP055858265
ANDERSEN WENDY C., SIEVERS ROBERT E., LAGALANTE ANTHONY F., BRUNO THOMAS J.: "Solubilities of Cerium(IV), Terbium(III), and Iron(III) β-Diketonates in Supercritical Carbon Dioxide", JOURNAL OF CHEMICAL AND ENGINEERING DATA., AMERICAN CHEMICAL SOCIETY., US, vol. 46, no. 5, 1 September 2001 (2001-09-01), US , pages 1045 - 1049, XP055858258, ISSN: 0021-9568, DOI: 10.1021/je000257c
SNEZHKO N. ET AL.: "Metal Chelates of Some β-Diketones as Volatile Precursors", MATERIALS SCIENCE AND ENGINEERING: B, vol. 18, no. 3, 15 April 1993 (1993-04-15), XP055834975, ISSN: 0921-5107, DOI: 10.1016/0921-5107(93)90137-C
HOLLAND W J, VEEL A E, GERRARD J: "3-Thianaphthenoyltrifluoroaeetone: A New Reagent for the Spectrophotometric Determination of Cerium(IV)", MIKROCHIMICA ACTA, vol. 58, 1 March 1970 (1970-03-01), pages 297 - 300, XP055858256, DOI: 10.1007/BF01221607
JAHR KARL HEINZ, GELIUS ROLF: "Metallchelate des Stearoylacetons", ZEITSCHRIFT FüR CHEMIE, WILEY, vol. 15, no. 7, 1 July 1975 (1975-07-01), pages 280 - 281, XP055834862, DOI: 10.1002/zfch.19750150715
DELAROSA MARK, BOUSMAN KENNETH, WELCH JOHN, TOSCANO PAUL: "Physical and Structural Characterization of Ce(IV) β -Diketonate Complexes: Evidence for Geometrical Isomers in the Solid-State", JOURNAL OF COORDINATION CHEMISTRY, TAYLOR & FRANCIS, LONDON, vol. 55, no. 7, 1 January 2002 (2002-01-01), London , pages 781 - 793, XP055834856, ISSN: 0095-8972, DOI: 10.1080/0095897022000001539
BRILL GISELA, MUSSO HANS: "Anisotropieeffekte in den 1H-NMR-Spektren 3-mesitylsubstituierter Acetylaceton-Metallchelate, II", LIEBIGS ANNALEN DER CHEMIE, vol. 1979, 29 June 1979 (1979-06-29), pages 803 - 810, XP055834980, DOI: 10.1002/jlac.197919790610
KASTNING E G, NAARMANN H, REIS H, BERDING C: "Metal Chelates as Polymerization Initiators", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 4, no. 4, 1 April 1965 (1965-04-01), pages 322 - 327, XP055858823, ISSN: 1521-3773, DOI: 10.1002/anie.196503221
BAXTER IAN ET AL.: "Preparation and Crystal Structures of the Ce(IV) β-Diketonates, [Ce(tmhd)4] and [Ce(pmhd)4] (Tmhd = 2, 2, 6, 6-Tetramethylheptane-3, 5-Dionate and Pmhd = 1-Phenyl-5-Methylhexane-1, 3-Dionate)", JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol. 28, no. 4, 1 April 1998 (1998-04-01), XP055834855, ISSN: 1572-8854
MCCARLEY R E, TEMPLETON J L, COLBURN T J, KATOVIC V, HOXMEIER R J, SHANKAR GOPALAN, RAMALINGAM SUTHAMALLI K: "Phenylisocyanation and Bromination Studies on Lanthanide Beta-Diketonates", TRANSITION METAL CHEMISTRY, vol. 9, no. 10, 1 December 1984 (1984-12-01), pages 449 - 453, XP055858268
TISCHER, ROBERT L, KENT J. EISENTRAUT KARL SCHELLER, ROBERT E. SIEVERS ROBERT C. BAUSMAN, PATRICIA R. BLUM: "New Rare Earth Antiknock Additives That are Potential Substitutes for Tetraethyl Lead (AD/A-O06 151)", AEROSPACE RESEARCH LABORATORIES - TECHNICAL REPORT, 1 December 1974 (1974-12-01), XP055858270
SCHILDCROUT STEVEN M: "Contribution from the Electron-Ionization Mass Spectra of Fluorinated Beta-Diketonate Complexes of Cerium(IV)+", INORGANIC CHEMISTRY, vol. 24, no. 5, 1 February 1985 (1985-02-01), pages 760 - 762, XP055858267
MUTHUKUMAR M, BALASUBRAMANIAN V: "Iodination, Bromination and Isocyanation Reactions of Beta-Diketonates of Lanthanum(III), Cerium(IV), Thorium(IV) and Uranyl(VI)", ASIAN JOURNAL OF CHEMISTRY, vol. 21, no. 1, 1 January 2009 (2009-01-01), pages 737 - 744, XP055858265
ANDERSEN WENDY C., SIEVERS ROBERT E., LAGALANTE ANTHONY F., BRUNO THOMAS J.: "Solubilities of Cerium(IV), Terbium(III), and Iron(III) β-Diketonates in Supercritical Carbon Dioxide", JOURNAL OF CHEMICAL AND ENGINEERING DATA., AMERICAN CHEMICAL SOCIETY., US, vol. 46, no. 5, 1 September 2001 (2001-09-01), US , pages 1045 - 1049, XP055858258, ISSN: 0021-9568, DOI: 10.1021/je000257c
SNEZHKO N. ET AL.: "Metal Chelates of Some β-Diketones as Volatile Precursors", MATERIALS SCIENCE AND ENGINEERING: B, vol. 18, no. 3, 15 April 1993 (1993-04-15), XP055834975, ISSN: 0921-5107, DOI: 10.1016/0921-5107(93)90137-C
HOLLAND W J, VEEL A E, GERRARD J: "3-Thianaphthenoyltrifluoroaeetone: A New Reagent for the Spectrophotometric Determination of Cerium(IV)", MIKROCHIMICA ACTA, vol. 58, 1 March 1970 (1970-03-01), pages 297 - 300, XP055858256, DOI: 10.1007/BF01221607
JAHR KARL HEINZ, GELIUS ROLF: "Metallchelate des Stearoylacetons", ZEITSCHRIFT FüR CHEMIE, WILEY, vol. 15, no. 7, 1 July 1975 (1975-07-01), pages 280 - 281, XP055834862, DOI: 10.1002/zfch.19750150715
Attorney, Agent or Firm:
ZHONGZI LAW OFFICE (CN)
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