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WO2001051533A1 - Compositions de revetement du bois polymerisables aux uv - Google Patents

Compositions de revetement du bois polymerisables aux uv Download PDF

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Publication number
WO2001051533A1
WO2001051533A1 PCT/US2001/000977 US0100977W WO0151533A1 WO 2001051533 A1 WO2001051533 A1 WO 2001051533A1 US 0100977 W US0100977 W US 0100977W WO 0151533 A1 WO0151533 A1 WO 0151533A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
woodcoat
weight
amount
photocurable
Prior art date
Application number
PCT/US2001/000977
Other languages
English (en)
Inventor
Roy C. Krohn
Original Assignee
Uv Specialties, Inc.
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 Uv Specialties, Inc. filed Critical Uv Specialties, Inc.
Priority to MXPA02006765A priority Critical patent/MXPA02006765A/es
Priority to CA002397140A priority patent/CA2397140A1/fr
Priority to AU2001229388A priority patent/AU2001229388A1/en
Priority to EP01942370A priority patent/EP1261655A1/fr
Publication of WO2001051533A1 publication Critical patent/WO2001051533A1/fr

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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/144—Polymers containing more than one epoxy group per molecule
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/145—Polyamides; Polyesteramides; Polyimides
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C09D163/10—Epoxy resins modified by unsaturated compounds
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00

Definitions

  • the present invention relates to ultraviolet light (uv) curable compositions capable of producing coating on a wood substrate on a wood substrate.
  • Wood surfaces on decks, teakwood boats, lumber (treated and untreated), and furniture are typically finished with transparent coatings to provide protection and enhance appearance.
  • lacquers containing cellulose compositions were often used to finish wood surfaces. Although inexpensive, these lacquers suffered from poor resistence to physical and chemical attack. Because of these shortcomings, cellulosic lacquers have been supplanted by heat curable coatings. Although more resistant to physical and chemical attack than the cellulosic lacquers, the heat curable coatings suffered from their own disadvantages.
  • Heat curable compositions require the use of organic solvents that contain a significant amount of volatile organic compounds (VOCs) . These VOCs escape into the atmosphere while the heat curable composition dries. Such solvent based systems are undesirable because of the hazards and expenses associated with VOCs. The hazards include water and air pollution and the expenses include the cost of complying with strict government regulation on solvent emission levels. In contrast, UV curable compositions contain reactive monomers instead of solvents; thus eliminating the detrimental effects of the VOCs
  • heat curable compositions not only raises environmental concerns but other disadvantages exist with their use. Heat curable suffer from slow cure times which lead to decreased productivity. These compositions require high energy for curing due to energy loss as well as the energy required to heat the coating. Additionally, many heat curable compositions yield poor film properties that result in decreased value of the end product.
  • UV curable compositions exhibit superior properties and performance over their heat curable counterparts
  • UV curable compositions themselves suffer from certain disadvantages.
  • UV compositions have high molecular weights and a substantial degree of cross linkage due to the highly reactive nature of the composition. As a result, many of these compositions suffer from low durability and resin shrinkage. With the use of many such compositions, an inordinately high amount of UV light is required to cure.
  • New formulations that lessen these problems typically suffer from diminished abrasion, chemical, and scratch resistance as well as low thermal stability and adhesion.
  • the present invention discloses an ultraviolet light curable woodcoat composition and method for making such a composition that may be used to produce a coating on a wood object.
  • the disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the active layer after curing.
  • the woodcoat composition contains 5 % or less volatile organic solvents by weight.
  • an ultraviolet light curable woodcoat composition comprises a mixture of one or more aliphatic acrylated oligomers, wherein the aliphatic acrylated oligomer mixture is present in an amount of about 10% to 40% of the woodcoat composition. All percentages of the woodcoat composition as expressed in this document refer to the weight percentage of the stated component to the total weight of the woodcoat composition in its fluid state at standard temperature and pressure.
  • the woodcoat composition preferably comprises an acrylated epoxy oligomer in an amount of about 5 % to 20 % , an isobornyl acrylate monomer in an amount of about 40% to 60% of the woodcoat composition, a photoinitiator in an amount of about 4% to 12% of the woodcoat composition, and a flow promoting agent in an amount of about 0.1 % to 8% of the woodcoat composition.
  • a method for depositing a woodcoat coating on a substrate.
  • the method comprises a first step of applying to the substrate a woodcoat fluid-phase composition ("woodcoat composition").
  • the woodcoat composition comprises a mixture of aliphatic acrylated oligomers, wherein the aliphatic acrylated oligomer is present in an amount of about 10% to 40% of the woodcoat composition.
  • the woodcoat composition also includes an acrylated epoxy oligomer in an amount of about 5 % to 20 % , an isobornyl acrylate monomer in an amount of about 40 % to 60 % of the woodcoat composition, a photoinitiator in an amount of about 4% to 12 % of the woodcoat composition, and a flow promoting agent in an amount of about 0. 1 % to 8 % of the woodcoat composition.
  • the method also includes a second step of illuminating the woodcoat composition on the substrate with an ultraviolet light to cause the woodcoat composition to cure into the woodcoat coating.
  • the woodcoat composition can be selectively deposited on the substrate at specific locations where woodcoat plating is desired. It need not be applied to the entire substrate.
  • a presently preferred ultraviolet light curable woodcoat composition (“woodcoat composition”) is provided.
  • the woodcoat composition includes a mixture of aliphatic acrylated oligomers.
  • the aliphatic acrylated oligomer mixture is present in an amount of about 10% to 40% of the woodcoat composition.
  • the aliphatic acrylated oligomer mixture is more preferably present in an amount of about 20% to 30% , and most preferably about 24% .
  • the aliphatic acrylated oligomer preferably comprises one or more urethane oligomers.
  • Suitable aliphatic acrylated oligomers include Radcure Ebecryl 244 (aliphatic urethane diacrylate diluted 10 % with 1 ,6-hexanediol diacrylate), Ebecryl 264 (aliphatic urethane triacrylate diluted 15 % with 1,6-hexanediol diacrylate), and Ebecryl 284 (aliphatic urethane diacrylate diluted 12 % with 1,6-hexanediol diacrylate) urethanes, commercially available from Radcure UCB Corp.
  • Radcure Ebecryl 244 aliphatic urethane diacrylate diluted 10 % with 1 ,6-hexanediol diacrylate
  • Ebecryl 264 aliphatic urethane triacrylate diluted 15 % with 1,6-hexanediol diacrylate
  • Ebecryl 284 aliphatic urethane diacrylate
  • Sartomer CN-961E75 (aliphatic urethane diacrylate blended with 25 % ethoxylated trimethylol propane triacylate), CN-961H81 (aliphatic urethane diacrylate blended with 19% 2(2-ethoxyethoxy)ethyl acrylate), CN-963A80 (aliphatic urethane diacrylate blended with 20% tripropylene glycol diacrylate), CN-964 (aliphatic urethane diacrylate), CN-966A80 (aliphatic urethane diacrylate blended with 20% tripropylene glycol diacrylate), CN-982A75 (aliphatic urethane diacrylate blended with 25 % tripropylene glycol diacrylate) and CN-983 (aliphatic urethane diacrylate), commercially available from Sartomer Corp.
  • the preferred aliphatic acrylated oligomers include Ebecryl 264 and Ebecryl 284.
  • Ebecryl 264 is an aliphatic urethane triacrylate supplied as an 85% solution in hexandiol diacrylate.
  • Ebecryl 284 is aliphatic urethane diacrylate of 1200 molecular weight diluted with 1,6-hexanediol diacrylate. Combinations of these materials may also be employed herein.
  • This preferred woodcoat composition further includes an acrylated epoxy oligomer.
  • the acrylated epoxy oligomer is present in an amount of about 5% to 20% .
  • the acrylated epoxy oligomer is more preferably present in an amount of about 8% to 16% , and most preferably about 12% .
  • Suitable acrylated epoxy oligomers include Radcure Ebecryl 3603 (novolac epoxy acrylate diluted 20 % with tripropylene glycol diacrylate), commercially available from Radcure UCB Corp. ; Sartomer CN-120 (difunctional bisphenol based epoxy acrylate) and CN124 (difunctional bisphenol based epoxy acrylate), commercially available from Sartomer Corp.
  • Echo Resin TME 9310 and 9345 commercially available from Echo Resins.
  • the preferred acrylated epoxy oligomer is Ebecryl 3603, which tri-functional acrylated epoxy novolac. Combinations of these materials may also be employed herein.
  • the preferred woodcoat composition also includes an isobornyl acrylate monomer in an amount of about 40 % to 60 % .
  • the isobornyl acrylate monomer is more preferably present in an amount of about 45 % to 55 % , and most preferably about 52% .
  • Suitable isobornyl acrylate monomers include Sartomer SR- 423 (isobornyl methacrylate):
  • Radcure IBOA isobornyl acrylate
  • IBOA and IBOMA commercially available from CPS Chemical
  • Genomer 1121 commercially available from Rahn Radiation Curing.
  • the preferred isobornyl acrylate monomers is Radcure IBOA, commercially available from Radcure Corp. Combinations of these materials may also be employed herein.
  • This preferred woodcoat composition also includes a photoinitiator in an amount of about 4% to 12% of the woodcoat composition.
  • the photoinitiator is more preferably present in an amount of about 6% to 10% , and most preferably about 8% .
  • Suitable photo initiators include Irgacure 184 (1-hydroxycyclohexyl phenyl ketone), Irgacure 907 (2-methyl-l-[4-(methylthio)phenyl]-2-morpholino propan- 1 -one) , Irgacure 369 (2-benzyl-2-N , N-dimethylamino- l -(4- morpholinophenyl)-l-butanone), Irgacure 500 (the combination of 1-hydroxy cyclohexyl phenyl ketone and 50% benzophenone), Irgacure 651 (2,2-dimethoxy-2- phenyl acetophenone), Irgacure
  • CYRACURE UVI-6974 mixed triaryl sulfonium hexafluoroantimonate salts
  • CYRACURE UVI-6990 mixed triaryl sulfonium hexafluorophosphate salts
  • the preferred photoinitiator is Irgacure 1700 commercially available from Ciba-Geigy of Tarrytown, New York. Combinations of these materials may also be employed herein.
  • the preferred woodcoat composition still further includes a flow promoting agent in an amount of about 0.1 % to 8 % , and preferably about 4.5 % , of the woodcoat composition.
  • Suitable flow promoting agents include Genorad 17, commercially available from Rahn Radiation Curing; and Modaflow, commercially available from Monsanto Chemical Co. , St. Louis, Missouri.
  • the preferred flow promoting agent is Modaflow which is an ethyl acrylate and 2-ethylhexyl acrylate copolymer that improves the flow of the composition. Combinations of these materials may also be employed herein.
  • This example provides a preferred woodcoat composition according to the invention.
  • the woodcoat composition was made from the following components:
  • the IBOA and Irgacure 1700 are mixed in a pan with a propeller blade mixer for 30 seconds at a speed of 500 to 1000 rpm.
  • the Ebecryl 264, the Ebecryl 284, the Ebecryl 3603, and Modaflow are introduced into the pan and mixed for 1 to 2 minutes at a speed of 2000 rpm. The mixing is temporarily suspended if the temperature exceed 100°F.
  • a method for depositing an woodcoat coating on a suitable substrate.
  • the method comprises a first step of applying a woodcoat fluid-phase composition ("woodcoat composition") to the substrate.
  • the woodcoat composition comprises a mixture of aliphatic acrylated oligomers, wherein the aliphatic acrylated oligomer is present in an amount of about 10% to 40% of the woodcoat composition.
  • the woodcoat composition also includes an acrylated epoxy oligomer in an amount of about 5% to 20% , an isobornyl acrylate monomer in an amount of about 40 % to 60 % of the woodcoat composition, a photoinitiator in an amount of about 4% to 12% of the woodcoat composition, and a flow promoting agent in an amount of about 0.1 % to 8% of the woodcoat composition.
  • the preferred woodcoat compositions according to this method are those described herein, for example, including the compositions described in example 1.
  • the woodcoat composition may be applied to the substrate using a number of different techniques.
  • the woodcoat composition may be applied, for example, by direct brush application, or it may be sprayed onto the substrate surface. It also may be applied using a screen printing technique.
  • screen printing technique a "screen" as the term is used in the screen printing industry is used to regulate the flow of liquid composition onto the substrate surface.
  • the woodcoat composition typically would be applied to the screen as the latter contacts the substrate.
  • the woodcoat composition flows through the silk screen to the substrate, whereupon it adheres to the substrate at the desired film thickness.
  • Screen printing techniques suitable for this purpose include known techniques, but wherein the process is adjusted in ways known to persons of ordinary skill in the art to accommodate the viscosity, flowability, and other properties of the liquid-phase composition, the substrate and its surface properties, etc.
  • Flexographic techniques for example, using pinch rollers to contact the woodcoat composition with a rolling substrate, also may be used.
  • the method includes a second step of illuminating the woodcoat fluid- phase composition on the substrate with an ultraviolet light to cause the woodcoat fluid-phase composition to cure into the woodcoat coating.
  • This illumination may be carried out in any number of ways, provided the ultraviolet light or radiation impinges upon the woodcoat composition so that the woodcoat composition is caused to polymerize to form the coating, layer, film, etc. , and thereby cures.
  • Curing preferably takes place by free radical polymerization, which is initiated by an ultraviolet radiation source.
  • the photoinitiator preferably comprises a photoinitiator, as described above.
  • ultraviolet light sources may be used, depending on the application.
  • Preferred ultraviolet radiation sources for a number of applications include known ultraviolet lighting equipment with energy intensity settings of, for example, 125 watts, 200 watts, and 300 watts per square inch.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention concerne une composition de revêtement du bois polymérisable à la lumière ultraviolette et un procédé d'obtention d'une telle composition s'utilisant dans la production d'un revêtement sur un objet en bois. Ces revêtements sont transparents et protègent l'objet en bois. La composition de l'invention ne contient pas une quantité significative de solvants organiques volatils qui ne soit pas incorporée dans la couche active après polymérisation.
PCT/US2001/000977 2000-01-13 2001-01-11 Compositions de revetement du bois polymerisables aux uv WO2001051533A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
MXPA02006765A MXPA02006765A (es) 2000-01-13 2001-01-11 Composiciones de revestimiento para madera, curables por luz ultravioleta.
CA002397140A CA2397140A1 (fr) 2000-01-13 2001-01-11 Compositions de revetement du bois polymerisables aux uv
AU2001229388A AU2001229388A1 (en) 2000-01-13 2001-01-11 Uv curable woodcoat compositions
EP01942370A EP1261655A1 (fr) 2000-01-13 2001-01-11 Compositions de revetement du bois polymerisables aux uv

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17597400P 2000-01-13 2000-01-13
US60/175,974 2000-01-13

Publications (1)

Publication Number Publication Date
WO2001051533A1 true WO2001051533A1 (fr) 2001-07-19

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/000977 WO2001051533A1 (fr) 2000-01-13 2001-01-11 Compositions de revetement du bois polymerisables aux uv

Country Status (5)

Country Link
EP (1) EP1261655A1 (fr)
AU (1) AU2001229388A1 (fr)
CA (1) CA2397140A1 (fr)
MX (1) MXPA02006765A (fr)
WO (1) WO2001051533A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003106124A1 (fr) 2002-06-13 2003-12-24 Armstrong World Industries, Inc. Procede de reduction de fissures superficielles de plancher composite revetu
EP2103297A1 (fr) 2008-03-20 2009-09-23 Ivoclar Vivadent AG Composition polymérisable contenant des initiateurs comprenant plusieurs atomes de Germanium
US7605190B2 (en) 2006-09-27 2009-10-20 Ivoclar Vivadent Ag Polymerizable compositions with acylgermanium compounds
DE102008047006A1 (de) 2008-09-12 2010-03-25 Heinrich-Heine-Universität Düsseldorf Lichthärtende Zusammensetzungen
WO2017055209A1 (fr) 2015-09-29 2017-04-06 Ivoclar Vivadent Ag Photoarmorceurs à base d'acyl-germanium et leur procédé de fabrication
EP3293215A1 (fr) 2016-09-07 2018-03-14 Ivoclar Vivadent AG Compositions polymérisables avec photoinitiateurs acylzinn
CN111662632A (zh) * 2020-05-20 2020-09-15 中牟县美林包装有限责任公司 一种包装箱局部逆向uv印刷方法
CN113621301A (zh) * 2021-08-23 2021-11-09 海南必凯水性新材料有限公司 一种环保水性漆、其制备方法及应用
EP4257592A1 (fr) 2022-04-08 2023-10-11 Evonik Operations GmbH Composés bisacyl digermanium, leur préparation et leur utilisation en tant que photo-initiateur de polymérisation radicalaire

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EP0530141A1 (fr) * 1991-08-22 1993-03-03 Ciba-Geigy Ag Composition durcissable par irradiation avec résistance contre l'huile à chaud
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US5596024A (en) * 1993-06-22 1997-01-21 Three Bond Co., Ltd. Sealing composition for liquid crystal
WO1997045458A1 (fr) * 1995-09-26 1997-12-04 Uv Coatings Limited Composition de finition durcissable a la lumiere ultraviolette et son procede d'utilisation
DE19835917A1 (de) * 1998-08-07 2000-02-10 Basf Ag Mit energischer Strahlung und/oder thermisch härtbare Bindemittel
WO2000062586A1 (fr) * 1999-04-14 2000-10-19 Allied Photochemical, Inc. Composition d'argent durcissable par ultraviolets et procede correspondant

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7381474B2 (en) 2002-06-13 2008-06-03 Awi Licensing Company Coated hardwood composite flooring having reduced surface cracking
US7537841B2 (en) 2002-06-13 2009-05-26 Awi Licensing Company Method and process to reduce surface cracking for coated hardwood composite flooring
WO2003106124A1 (fr) 2002-06-13 2003-12-24 Armstrong World Industries, Inc. Procede de reduction de fissures superficielles de plancher composite revetu
US7605190B2 (en) 2006-09-27 2009-10-20 Ivoclar Vivadent Ag Polymerizable compositions with acylgermanium compounds
US8829067B2 (en) 2008-03-20 2014-09-09 Ivoclar Vivadent Ag Polymerizable compositions with initiators containing several Ge atoms
EP2103297A1 (fr) 2008-03-20 2009-09-23 Ivoclar Vivadent AG Composition polymérisable contenant des initiateurs comprenant plusieurs atomes de Germanium
DE102008047006A1 (de) 2008-09-12 2010-03-25 Heinrich-Heine-Universität Düsseldorf Lichthärtende Zusammensetzungen
WO2017055209A1 (fr) 2015-09-29 2017-04-06 Ivoclar Vivadent Ag Photoarmorceurs à base d'acyl-germanium et leur procédé de fabrication
EP3293215A1 (fr) 2016-09-07 2018-03-14 Ivoclar Vivadent AG Compositions polymérisables avec photoinitiateurs acylzinn
WO2018046438A1 (fr) 2016-09-07 2018-03-15 Ivoclar Vivadent Ag Compositions polymérisables à photoamorceurs acylétain
CN111662632A (zh) * 2020-05-20 2020-09-15 中牟县美林包装有限责任公司 一种包装箱局部逆向uv印刷方法
CN113621301A (zh) * 2021-08-23 2021-11-09 海南必凯水性新材料有限公司 一种环保水性漆、其制备方法及应用
EP4257592A1 (fr) 2022-04-08 2023-10-11 Evonik Operations GmbH Composés bisacyl digermanium, leur préparation et leur utilisation en tant que photo-initiateur de polymérisation radicalaire

Also Published As

Publication number Publication date
CA2397140A1 (fr) 2001-07-19
EP1261655A1 (fr) 2002-12-04
MXPA02006765A (es) 2005-07-01
AU2001229388A1 (en) 2001-07-24

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