Classifications

• • 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
• • 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
  • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• • 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
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/10—Printing inks based on artificial resins
  • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing

Definitions

• - phenyl, C1-C8alkyl both being unsubstituted or substituted by -OH, -Oalkyl, C2-C8acyloxy, -NR 8 R 9 , -COOalkyl or CN;
• -R 1 is selected from hydrogen, C1-C8 alkyl which is unsubstituted or substituted by C2-C8acyloxy, -NR 8 R 9 , -COOalkyl; or -CN, or R 1 represents C3-C5alkenyl, C5-C12cycloalkyl, phenyl and benzyl;
• the invention relates to the use of the compounds of formula (la) and (II), as above defined, as photoinitiators. According to another of its aspects the invention relates to a process for photocuring comprising at least one of compounds of formula (I), (la) and (II), and to an article of manufacture made by said process.
• phenyl substituted with one or more electron donating groups said electrodonating groups being preferably selected from one or more OH, C1-C18 alkyl, -Oalkyl, - Oalkoxy, -Ophenyl, -SH, - Salkyl, -Salkoxy, -Sphenyl, -SO 2 alkyl, -SO 2 alkoxy, -SO 2 phenyl, - COOalkyl, SO 2 NH 2 , -SO 2 NHaikyl, -SO 2 N(alkyl) 2 , -NHalkyl, - NHalkoxy, - N(alkyl) 2 , morfolino, piperidino, piperazino, - N(alkoxy) 2 , -NHCOalkyl or -NHCOphenyl or represents thienyl, 2-methyithienyl, pyrryl, furyl, indanyl, imidazolyl, thiazo
• arylene-T-arylenes are preferably selected from phenylene-T- phenylenes such as diphenylmethane, diphenylether and diphenylsulfide; and a trimethyl-phenyl-indane group such as the one of formula
• C1-C18 alkyl is selected from a linear or branched, saturated alkyl, which can be unsubstituted or substituted by aryl, alkyl, aryloxy, alkoxy, heteroatoms and/or heterocyclic groups, and includes, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert- butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, decyl, dodecyl, tetradecyl, heptadecyl, octadecyl, 1,1-dimethylpropyl, 1,1-dimethylbutyl, 1,1,3,3-tetramethylbutyl, benzyl, 1-phenylethyl, 2-phenyl-ethyl, a,a
• an amine-modified acrylate compound can be used as the amine accelerators/co-initiators: examples of such amine-modified acrylate include acrylates modified by reaction with a primary or secondary amine that are described in US 3,844,916, EP 280222, US 5,482,649 or US 5,734,002. Multifunctional amine and polymeric amine derivatives are also suitable as co-initiators some examples are Omnipol ® ASA from IGM Resins B.V., Genopol ® AB-2 from Rahn A.G., Speedcure ® 7040 from Lambson Limited or those described in US2013/0012611.
• Step 2 To a suspension of Nal (5.98 g, 39.93 mmol) in acetonitrile (50 mL) a solution of 6-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (prepared in step 1) (4.97 g, 28.52 mmol) in acetonitrile (10mL) was added followed by triethylamine (5.95 mL 42.78 mmol). Then the mixture was cooled to 0°C and chlorotrimethyisilane (4.71 mL, 37.08 mmol) was added dropwise. Mixture was stirred under nitrogen at room temperature for two hours.
• a-disilyloxyketones of the invention were compared with 2-methyl-2- (1,1,2,2,2-pentamethyldisilyloxy)-1-phenylpropan-1-one (COMP-1) of the prior art prepared as described in Macromolecules 2009, 42, 6031-6037 (PI-1) and 2-hydroxy-2-methyl-1-phenylpropanone (COMP-2).
• the photopolymerizable compositions for the test were prepared dissolving the photoinitiators at a concentration of 3% by weight (wt) each in a mixture 99.5:0.5 wt of Ebecryl ® 605 and Ebecryl ® 350 (Allnex).

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Polymers & Plastics (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Polymerisation Methods In General (AREA)
• Indole Compounds (AREA)
• Adhesives Or Adhesive Processes (AREA)
• Plural Heterocyclic Compounds (AREA)

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Citations (27)

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• 2019
  • 2019-12-20 WO PCT/IB2019/061152 patent/WO2020136522A1/en not_active Ceased
  • 2019-12-20 JP JP2021538138A patent/JP7472429B2/ja active Active
  • 2019-12-20 CN CN201980093237.XA patent/CN113518805B/zh active Active
  • 2019-12-20 US US17/296,343 patent/US11834532B2/en active Active
  • 2019-12-20 KR KR1020217023813A patent/KR102888120B1/ko active Active
  • 2019-12-20 EP EP19856418.9A patent/EP3902878B1/en active Active

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