CA2022587A1 - Mono- and di-acylphosphine oxides - Google Patents

Mono- and di-acylphosphine oxides

Info

Publication number
CA2022587A1
CA2022587A1 CA2022587A CA2022587A CA2022587A1 CA 2022587 A1 CA2022587 A1 CA 2022587A1 CA 2022587 A CA2022587 A CA 2022587A CA 2022587 A CA2022587 A CA 2022587A CA 2022587 A1 CA2022587 A1 CA 2022587A1
Authority
CA
Canada
Prior art keywords
mono
acylphosphine oxides
formula
compounds
photopolymerization
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.)
Granted
Application number
CA2022587A
Other languages
French (fr)
Other versions
CA2022587C (en
Inventor
Werner Rutsch
Kurt Dietliker
Roger Graham Hall
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.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of CA2022587A1 publication Critical patent/CA2022587A1/en
Application granted granted Critical
Publication of CA2022587C publication Critical patent/CA2022587C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3247—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
    • C07F9/3252—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se) containing the structure -C(=X)-P(=X)(R)(XR), (X = O, S, Se)
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polymerisation Methods In General (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)

Abstract

Compounds of the formula I
(see formula I) in which at least one of the radicals R1, R2 and R3 is a substituted alkyl radical or cycloalkyl radical, or R1 and R2 together with the phosphorus atom form a monocyclic or tricyclic ring, are effective photoinitiators for the photopolymerization of ethylenically unsaturated compounds.
CA002022587A 1989-08-04 1990-08-02 Mono- and di-acylphosphine oxides Expired - Fee Related CA2022587C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH289789 1989-08-04
CH2897/89-8 1989-08-04

Publications (2)

Publication Number Publication Date
CA2022587A1 true CA2022587A1 (en) 1991-02-05
CA2022587C CA2022587C (en) 2000-12-05

Family

ID=4244067

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002022587A Expired - Fee Related CA2022587C (en) 1989-08-04 1990-08-02 Mono- and di-acylphosphine oxides

Country Status (8)

Country Link
EP (2) EP0736540A3 (en)
JP (1) JP2973130B2 (en)
KR (1) KR0168328B1 (en)
CA (1) CA2022587C (en)
DD (1) DD298405A5 (en)
DE (1) DE59010615D1 (en)
ES (1) ES2098260T3 (en)
RU (2) RU2071610C1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014016567A1 (en) 2012-07-24 2014-01-30 Lambson Limited Photopolymerisation processes and novel compounds therefor

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DE59307404D1 (en) * 1992-03-11 1997-10-30 Ciba Geigy Ag Benzoyl substituted phosphabicycloalkanes and sulfides as photoinitiators
ES2059261B1 (en) * 1992-10-08 1995-11-16 Ciba Geigy Ag ALKYL-BISACILPHOSPHINOXIDES.
DE4302123A1 (en) * 1993-01-27 1994-07-28 Herberts Gmbh Printing glass hollow-ware esp. bottle with ink contg. organic binder
CA2134156A1 (en) * 1993-11-22 1995-05-23 Thomas P. Klun Coatable compositions, abrasive articles made therefrom, and methods of making and using same
JPH08171209A (en) * 1994-12-15 1996-07-02 Japan Synthetic Rubber Co Ltd Radiation curable composition
US5707781A (en) * 1995-05-05 1998-01-13 Bayer Corporation Photopolymerizable compositions having acyl or diacyl phosphine oxide and a fluorescent optical brightner
DE69710657T3 (en) * 1996-08-23 2007-07-05 Showa Denko K.K. Photohardenable composition and curing process
SG53043A1 (en) * 1996-08-28 1998-09-28 Ciba Geigy Ag Molecular complex compounds as photoinitiators
HUP0101680A3 (en) 1998-03-13 2005-09-28 Akzo Nobel Nv Non-aqueous coating compositions based on an oxidatively drying alkyd resins and process for producing this alkyd resins
GB2360283B (en) * 2000-02-08 2002-08-21 Ciba Sc Holding Ag Monoacylarylphosphines and acylphosphine oxides and sulphides
GB2365430B (en) * 2000-06-08 2002-08-28 Ciba Sc Holding Ag Acylphosphine photoinitiators and intermediates
CA2467576A1 (en) 2001-11-20 2003-05-30 Jean-Pierre Wolf Multimer forms of acylphosphines and their derivatives
DE10205191C1 (en) * 2002-02-08 2003-10-09 Hobas Engineering Gmbh Klagenf Multi-layer plastic tube manufactured using the centrifugal process
EP1511754B1 (en) 2002-06-11 2008-07-23 Ciba Holding Inc. Multimer forms of mono- and bis-acylphosphine oxides
DE602005025217D1 (en) * 2004-04-15 2011-01-20 Basf Se PROCESS FOR PHOTO-PAINTING WITH LIGHT-EMITTING DIODES
US20090137771A1 (en) * 2005-08-11 2009-05-28 Satoshi Moriyama Resin composition
US7465819B2 (en) 2006-01-24 2008-12-16 Chung Shan Institute Of Science And Technology Bisbiphenylacylphosphine oxide and preparation method therefore
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014016567A1 (en) 2012-07-24 2014-01-30 Lambson Limited Photopolymerisation processes and novel compounds therefor

Also Published As

Publication number Publication date
JP2973130B2 (en) 1999-11-08
RU2071610C1 (en) 1997-01-10
RU2057759C1 (en) 1996-04-10
EP0413657B1 (en) 1996-12-27
EP0736540A2 (en) 1996-10-09
KR0168328B1 (en) 1999-03-20
EP0736540A3 (en) 1997-06-18
JPH03101686A (en) 1991-04-26
DE59010615D1 (en) 1997-02-06
ES2098260T3 (en) 1997-05-01
EP0413657A2 (en) 1991-02-20
CA2022587C (en) 2000-12-05
DD298405A5 (en) 1992-02-20
EP0413657A3 (en) 1992-03-18
KR910004641A (en) 1991-03-29

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